- Design And Synthesis Of An Azabicyclic Nucleoside Phosphoramidite For Oligonucleotide Antisense Constructs
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We report the synthesis and biophysical evaluation of an azabicycle dinucleotide with restricted γ, β, and ε torsion angles, featuring the introduction of a piperidine ring that locks the conformation of the nucleoside into an RNA-type nucleic acid. The c
- Salinas, Juan C.,Seth, Punit P.,Hanessian, Stephen
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- 3-Azidoazetidines as the first scaffolds for β-amino azetidine carboxylic acid peptidomimetics: azetidine iminosugars containing an acetamido group do not inhibit β-N-acetylhexosaminidases
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Stable amides and oligopeptides derived from methyl trans,trans-3-azido-4-hydroxymethyl-L-azetidine carboxylate, prepared in 19% yield from diacetone allose, is the first example of a β-amino-azetidine carboxylic acid incorporated into peptidomimetics and provides a scaffold for investigating secondary structure induced by a novel β-amino acid. A number of azetidine iminosugars containing a NHAc substituent were prepared but none of them were β-N-acetylhexosaminidase inhibitors.
- Liu, Zilei,Jenkinson, Sarah F.,Kato, Atsushi,Nakagawa, Shinpei,Wormald, Mark R.,Yu, Chu-Yi,Fleet, George W.J.
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- An efficient method to synthesize novel 5-O-(6′-modified)-mycaminose 14-membered ketolides
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A new and facile procedure was developed to synthesize novel 5-O-(6′-modified)-mycaminose 14-membered ketolides by adopting different protective strategies and comparing various glycosylation conditions. Seven trichloroacetimidate donors which had different types of substituent groups at C-6 position were synthesized to couple with the erythronolide. Nine novel 5-O-(6′-modified)-mycaminose 14-membered ketolides were obtained to verify the utility of the method.
- Wang, A-Peng,Liu, Chao,Yang, Shuang,Zhao, Zhehui,Lei, Pingsheng
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Read Online
- Gabriel-Cromwell aziridination of amino sugars; chiral ferrocenoyl-aziridinyl sugar synthesis and their biological evaluation
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N-sugar substituted chiral aziridines were synthesized via Gabriel-Cromwell reaction. Novel pure diastereomers of aziridine derivatives (4 diastereomers) were readily obtained in high yields and their structures were confirmed by means of 1H NM
- Sert, Mustafa,I??lar, ?zer,Yaglioglu, Ayse Sahin,Bulut, Adnan
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- Synthesis and biological evaluation of novel urea, thiourea and squaramide diastereomers possessing sugar backbone
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A series of novel chiral 14 urea, thiourea and squaramide stereoisomers possessing carbohydrate backbones as well as amide functional groups was synthesized and characterized by their, 1H NMR, 13C NMR, FT-IR, HRMS, optical rotation, and melting points. Their antiproliferative activities were investigated against HeLa and PC3 cell lines. The compounds 9, 11 and 12 showed better activities at 25 μM against PC3 cell line with respect to the standard 5-fluorouracil (5-FU). Especially, the compounds 9 and 11 showed higher activities than the standard 5-FU even at low concentration (5 μM) against HeLa cell line. IC50 results also confirm these activities. The compounds 9, 10 and 11 have the IC50 values of 1.10 μM, 1.51 μM and 1.02 μM, respectively while 5-FU has 2.51 μM. Moreover, their cytotoxicity tests have proven that their viabilities were in between 50% and 100%.
- Arat, Esra,Bulut, Adnan,Demirta?, ?brahim,I??lar, ?zer,Sahin Yaglioglu, Ayse,Türk, Mustafa
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- Multicomponent Approach to Homo-and Hetero-Multivalent Glycomimetics Bearing Rare Monosaccharides
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We applied a multicomponent approach to access a library of densely functionalized homo-and hetero-multivalent glycomimetics comprising aldehyde, amine, and isocyanide components related to isopropylidene-protected d-fructose, l-sorbose, d-galactose, and d-Allose. Passerini products were obtained in very good yields (up to 78%) and high diastereoselectivities (up to 98:2). Three types of products were obtained by the Ugi reaction; along with the "classical" four-component product, α-Acylaminoamides, a three-component α-Aminoamides, and a four-component α-Aminoacylamides were isolated. The presence of multiple pathways is rationalized by the structure of the imidate intermediate, mainly influenced by the amine component.
- Jakas, Andreja,Jeri?, Ivanka,Vi?njevac, Aleksandar
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p. 3766 - 3787
(2020/03/30)
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- A method for preparing N-alkylated kanosamines from diacetone D-glucose
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The aminoglycoside (AG) antibiotics have seen a resurgence in their clinical use given the increase in multi drug resistant bacterial infections. Campaigns to generate novel analogs show promise that structural modification can lead to compounds with improved pharmacological properties. The results described herein include a new method to synthesize mono-, di-, and mixed N-alkylated kanosamine sugars and their elaboration into novel glycosides that inhibit bacterial protein synthesis in vitro.
- Cannone, Zachary P.,Peczuh, Mark W.
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p. 1830 - 1833
(2019/06/19)
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- Cluster glycosides and heteroglycoclusters presented in alternative arrangements
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Multivalent carbohydrates, or glycoclusters, are useful tools to study glycan-lectin and glycan-enzyme recognition processes and have wide potential therapeutic applicability. Herein, we report the synthesis of novel glycoclusters presenting glucopyranose
- Figueredo, Andreza S.,Zamoner, Luis O.B.,Rejzek, Martin,Field, Robert A.,Carvalho, Ivone
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p. 4405 - 4409
(2018/11/10)
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- Synthesis of triazolylmethyl-linked nucleoside analogs via combination of azidofuranoses with propargylated nucleobases and study on their cytotoxicity
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[Figure not available: see fulltext.] Copper(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition reactions (CuAAC) between azidofuranoses and propargyl-nucleobases were carried out in the presence of CuSO4·5H2O and sodium ascorbate as catalytic system to provide the corresponding 1,4-disubstituted-1,2,3-triazole-bridged nucleoside analogs in good yields. Twelve new sugar-based triazolylmethyl-linked nucleoside analogs were synthesized and screened for their cytotoxic activity against MDA-MB-231, Hep3B, PC-3, SH-SY5Y, and HCT-116 cancer cell lines and control cell line (L929). Most of the compounds were moderately effective against all the cancer cell lines assayed. Particularly, among the tested compounds, 1,2,3-triazole-linked 5-fluorouracil–mannofuranose hybrid was found to be the most potent cytotoxic agent against HCT-116, Hep3B, SH-SY5Y cells with IC50 values of 35.6, 71.1, and 75.6 μM, respectively. None of the triazolylmethyl-linked nucleoside analogs exhibited cytotoxic effect against the control cells L929.
- Halay, Erkan,Ay, Emriye,?alva, Emine,Ay, Kadir,Karay?ld?r?m, Tamer
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p. 158 - 166
(2018/04/02)
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- C-3 epimers of sugar amino acids as foldameric building blocks: improved synthesis, useful derivatives, coupling strategies
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To obtain key sugar derivatives for making homooligomeric foldamers or α/β-chimera peptides, economic and multigram scale synthetic methods were to be developed. Though described in the literature, the cost-effective making of both 3-amino-3-deoxy-ribofuranuronic acid (H–tX–OH) and its C-3 epimeric stereoisomer, the 3-amino-3-deoxy-xylofuranuronic acid (H–cX–OH) from d-glucose is described here. The present synthetic route elaborated is (1) appropriate for large-scale synthesis; (2) reagent costs reduced (e.g. by a factor of 400); (3) yields optimized are ~80% or higher for all six consecutive steps concluding –tX– or –cX– and (4) reaction times shortened. Thus, a new synthetic route step-by-step optimized for yield, cost, time and purification is given both for d-xylo and d-ribo-amino-furanuronic acids using sustainable chemistry (e.g. less chromatography with organic solvents; using continuous-flow reactor). Our study encompasses necessary building blocks (e.g. –X–OMe, –X–OiPr, –X–NHMe, Fmoc–X–OH) and key coupling reactions making –Aaa–tX–Aaa– or –Aaa–tX–tX–Aaa– type “inserts”. Completed for both stereoisomers of X, including the newly synthesized Fmoc–cX–OH, producing longer oligomers for drug design and discovery is more of a reality than a wish.
- Nagy, Adrienn,Csordás, Barbara,Zsoldos-Mády, Virág,Pintér, István,Farkas, Viktor,Perczel, András
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p. 223 - 240
(2017/02/05)
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- Organocatalyzed asymmetric Michael addition by an efficient bifunctional carbohydrate-thiourea hybrid with mechanistic DFT analysis
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A series of thiourea based bifunctional organocatalysts having d-glucose as a core scaffold were synthesized and examined as catalysts for the asymmetric Michael addition reaction of aryl/alkyl trans-β-nitrostyrenes over cyclohexanone and other Michael donors having active methylene. Excellent enantioselectivities (0. The obtained results were explained through DFT calculations using the B3LYP/6-311G(d,p)//B3LYP/6-31G(d) basic set. The QM/MM calculations revealed the role of cyclohexanone as a solvent as well as reactant in the rate determining step imparting 31.91 kcal mol?1 of energy towards the product formation.
- Azad, Chandra S.,Khan, Imran A.,Narula, Anudeep K.
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p. 11454 - 11461
(2016/12/18)
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- Glucose positions affect the phloem mobility of glucose-fipronil conjugates
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In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.
- Lei, Zhiwei,Wang, Jie,Mao, Genlin,Wen, Yingjie,Tian, Yuxin,Wu, Huawei,Li, Yufeng,Xu, Hanhong
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p. 6065 - 6071
(2015/04/22)
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- Synthesis of 3,3′-neotrehalosadiamine and related 1,1′-aminodisaccharides using disarmed, armed, and superarmed building blocks
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Here we report a high yielding, stereoselective synthesis of the naturally occurring 1,1′-disaccharide neotrehalosadiamine (NTD) and some related analogs. Following an eleven-step sequence, seven of which did not require chromatographic separation, NTD was generated in 60% overall yield from the inexpensive, commercially available precursor 1,2:5,6-di-O-isopropylidene- α-δ-glucofuranose. The key a,b-linkage of NTD was formed in a highly stereoselective manner by taking advantage of the participating effect of the acyl group at O-2 of the donor glycoside. The influence of electronic effects of disarmed, armed, and superarmed glycosyl donors and acceptors on the outcome of 1,1′-glycosidation was also observed. Antibacterial studies using NTD and its analogs show detectable but weak antistaphylococcal activity.
- Anjum, Shazia,Vetter, Natasha D.,Rubin, Joseph E.,Palmer, David R.J.
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p. 816 - 825
(2013/07/25)
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- Stereocontrolled facile synthesis and biological evaluation of (3 S) and (3 R)-3-Amino (and Azido)-3-deoxy pyranonucleosides
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This article describes the synthesis of (3 S) and (3 R)-3-amino-3-deoxy pyranonucleosides and their precursors (3 S) and (3 R)-3-azido-3-deoxy pyranonucleosides. Azidation of 1,2:5,6-di-O-isopropylidene-3-O-toluenesulfonyl- α-D-allofuranose followed by hy
- Manta, Stella,Parmenopoulou, Vanessa,Kiritsis, Christos,Dimopoulou, Athina,Kollatos, Nikolaos,Papasotiriou, Ioannis,Balzarini, Jan,Komiotis, Dimitri
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experimental part
p. 522 - 535
(2012/10/08)
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- Design and synthesis of regioisomeric triazole based peptidomimetic macrocycles and their dipole moment controlled self-assembly
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Two peptidomimetic macrocycles, regioisomeric in terms of the position of triazole/amide, have been synthesized. Both undergo self-assembly in a parallel manner but in solvents of opposite polarity, ascribed to (β, β) and (β-D, β-L) hydrogen bonding leading to formation of two different unique classes of organic nanostructures. The Royal Society of Chemistry.
- Ghorai, Abhijit,Padmanaban,Mukhopadhyay, Chaitali,Achari, Basudeb,Chattopadhyay, Partha
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supporting information
p. 11975 - 11977
(2013/01/16)
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- Synthesis and antibacterial activity of aminodeoxyglucose derivatives against Listeria innocua and Salmonella typhimurium
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In this study aminodeoxyglucose derivatives were synthesized and evaluated for their antibacterial activity against two food bacteria, Listeria innocua and Salmonella typhimurium. 6-Amino-6-deoxy-α-Dmethylglucopyranose (GSA-6), 3-amino-3-deoxy-D-glucopyranoside (GSA-3), and β-D-glucopyranosylamine (GSA-1) were synthesized and concurrently tested with commercially available D-glucosamine (GSA-2) for antibacterial activity. Results obtained from this study showed a pronounced antagonist effect due to the position of amino groups of aminoglucose derivatives on the antibacterial activity. GSA-3 was the most active compound. At a concentration of 2 × 10 -4 mol mL -1, it delayed the growth of both bacteria with percentages of inhibition of 29 and 15% for L. innocua and S. typhimurium, respectively. At the same concentration the percentages of inhibition for other aminodeoxyglucoses varied between 5 and 18% and between 2 and 11% for L. innocua and S. typhimurium, respectively. All compounds were characterized by FTIR, 1H NMR, and 13C NMR spectroscopy.
- Theoneste, Muhizi,Stephane, Greller,Veronique, Coma
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experimental part
p. 8770 - 8775
(2010/07/17)
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- Modular furanoside phosphite-phosphoroamidites, a readily available ligand library for asymmetric palladium-catalyzed allylic substitution reactions. Origin of enantioselectivity
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A library of furanoside phosphite-phosphoroamidite ligands has been synthesized and screened in the palladium-catalyzed allylic substitution reactions of several substrate types. These series of ligands can be prepared efficiently from easily accessible D
- Raluy, Eva,Pamies, Oscar,Dieguez, Montserrat
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scheme or table
p. 1648 - 1670
(2011/03/18)
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- Monosaccharide Derivatives as Anti-Inflammatory and/or Anti-Cancer Agents
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The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disorder herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases su
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Page/Page column 17
(2009/03/07)
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- Synthesis of UDP-glucose derivatives modified at the 3-OH as potential chain terminators of β-glucan biosynthesis
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A series of UDP-d-glucose derivatives and precursors that have been modified at C-3 were synthesised from d-glucose as potential chain terminators of β-glucan biosynthesis. None of the UDP-derivatives or the precursors tested displayed significant anti-fungal activity in a series of germination assays on the dermatophyte Trichophyton rubrum.
- Danac, Ramona,Ball, Lucy,Gurr, Sarah J.,Fairbanks, Antony J.
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p. 1012 - 1022
(2008/09/20)
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- Chemoenzymatic synthesis of GDP-azidodeoxymannoses: Non-radioactive probes for mannosyltransferase activity
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GDP-2-, 3-, 4- or 6-azidomannoses can be successfully prepared from the corresponding azidomannose-1-phosphates and GTP using the enzyme GDP-Mannosepyrophosphorylase (GDP-ManPP) from Salmonella enterica and may serve as useful probes for mannosyltransferase activity. The Royal Society of Chemistry.
- Marchesan, Silvia,Macmillan, Derek
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supporting information; scheme or table
p. 4321 - 4323
(2009/03/12)
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- MONOSACCHARIDE DERIVATIVES
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The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disorder herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases su
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Page/Page column 18
(2008/12/05)
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- Model for antibiotic optimization via neoglycosylation: Synthesis of liponeoglycopeptides active against VRE
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The neoglycosylation of a methoxyamine-appended vancomycin aglycon with all possible N′-decanoylglucopyranose and N′-biphenoylglucopyranose regioisomers led to the production of a focused set of liponeoglycopeptide variants in good yields and with excellent stereoselectivity. High-throughput antibacterial assays employing a unique set of vancomycin-resistant Enterococci faecalis and Enterococci faecium clinical isolates revealed that the nature and regiochemistry of glycosyl lipidation modulated vancomycin-resistent Enterococci potency. In contrast to prior work with lipoglycopeptides, this study reveals the glucose C3′ or C4′ as the optimal position for neoglycopeptide lipidation. This purely chemical method for the diversification of the glycolipid portion of lipoglycopeptide antibiotics is simple to perform on a large scale, requires minimal synthetic effort in sugar donor preparation, and provides access to highly active antibiotics that are not easily prepared by other state-of-the-art methods.
- Griffith, Byron R.,Krepel, Candace,Fu, Xun,Blanchard, Sophie,Ahmed, Aqeel,Edmiston, Charles E.,Thorson, Jon S.
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p. 8150 - 8155
(2008/02/11)
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- MONOSACCHARIDE DERIVATIVES AS ANTI-INFLAMMATORY AND/OR ANTI-CANCER AGENTS
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The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disorder herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases su
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Page/Page column 25
(2010/11/28)
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- A general strategy for the stereoselective synthesis of l-1-deoxyallonojirimycin and d-1-deoxygulonojirimycin
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A general strategy for the synthesis of deoxyazasugars from d-glucose is described. Ring-closing metathesis and stereoselective dihydroxylation reactions were used as key steps.
- Ghosh, Subhash,Shashidhar,Dutta, Samit Kumar
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p. 6041 - 6044
(2007/10/03)
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- MONOSACCHARIDE DERIVATIVES AS ANTI-INFLAMMATORY AND/OR ANTI-CANCER AGENTS
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The present invention relates to monosaccharide derivatives as anti-inflammatory agents. The compounds disorder herein can be useful for inhibition and prevention of inflammation and associated pathologies including inflammatory and autoimmune diseases su
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Page/Page column 37
(2010/11/24)
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- Kanosamine biosynthesis: A likely source of the aminoshikimate pathway's nitrogen atom
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The biosynthetic source of the nitrogen atom incorporated into the aminoshikimate pathway has remained a question for some time. 3-Amino-3-deoxy-d-fructose 6-phosphate has previously been demonstrated to be a precursor to 4-amino-3,4-dideoxy-d-arabino-heptulosonic acid 7-phosphate and 3-amino-5-hydroxybenzoic acid via the inferred intermediacy of 1-deoxy-1-imino-d-erythrose 4-phosphate in Amycolatopsis mediterranei cell-free extract. This investigation examines the possibility that the natural product kanosamine might be a precursor to 3-amino-3-deoxy-d-fructose 6-phosphate. Kanosamine 6-phosphate was synthesized by a chemoenzymatic route and incubated in A. mediterranei cell-free lysate along with d-ribose 5-phosphate and phosphoenolpyruvate. Formation of 4-amino-3,4-dideoxy-d-arabino-heptulosonic acid 7-phosphate and 3-amino-5-hydroxybenzoic acid was observed. Subsequent incubation in A. mediterranei cell-free lysate of glutamine and NAD with UDP-glucose resulted in the formation of kanosamine. The bioconversion of UDP-glucose into kanosamine along with the bioconversion of kanosamine 6-phosphate into 4-amino-3,4-dideoxy-d-arabino-heptulosonic acid 7-phosphate and 3-amino-5-hydroxybenzoic acid suggests that kanosamine biosynthesis is the source of the aminoshikimate pathway's nitrogen atom. Copyright
- Guo, Jiantao,Frost
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p. 10642 - 10643
(2007/10/03)
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- An Alternative Synthesis of the Antineoplastic Nucleoside 4′-ThioFAC and Its Application to the Synthesis of 4′-ThioFAG and 4′-Thiocytarazid
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Previously, we synthesized 4′-thioFAC, a novel antineoplastic cytosine nucleoside, by developing an original method. However, several problems remained. To overcome these problems, we have developed an alternative method for the synthesis of 4′-thionucleosides. In the original synthesis, carbons from C1 to C5 of D-glucose were used. The new method also starts from D-glucose but uses carbons closer to the tail (C2-C6). A dibenzoyl derivative obtained by this approach was brominated at the anomeric position to give a 1-bromide derivative. Fusion of the 1-bromide and persilylated acetylcytosine, followed by deprotection, predominantly gave a β-anomer of 4′-thioFAC. The reaction of 2,6-diaminopurine with the 1-bromide in the presence of TMS triflate gave a glycosylated product in good yield. After deprotection, the resulting 1:1 anomeric mixture of free nucleosides was treated with adenosine deaminase to give a β-anomer of 4′-thioFAG, a guanine congener of 4′-thioFAC, selectively. Using a similar approach, we synthesized 4′-thiocytarazid, which was not possible using the original method.
- Yoshimura, Yuichi,Endo, Mikari,Miura, Shinji,Sakata, Shinji
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p. 7912 - 7920
(2007/10/03)
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- N-azole substituted carbohydrates. Synthesis and transformations of 1- (3'-deoxy-1',2':5',6'-di-O-isopropylidene-α-D-glucofuranos-3'-yl)-azole derivatives
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The synthesis and chemical manipulation of some 1-(3'-deoxy-1',2':5',6'- di-O-isopropylidene-α-D-glucofuranos-3'-yl)-azole derivatives is described.
- Marco-Contelles, Jose,Jimenez
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p. 10511 - 10526
(2007/10/03)
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- 3-Azidotetrahydrofuran-2-carboxylates: Monomers for five-ring templated β-amino acid foldamers?
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Four diastereomeric methyl 3-azidotetrahydrofuran-2-carboxylates were prepared from diacetone glucose as precursors for the synthesis of β-amino acid oligomers with secondary structure.
- Watterson, Mark P.,Pickering, Lea,Smith, Martin D.,Hudson, Sarah J.,Marsh, Paul R.,Mordaunt, Jacqueline E.,Watkin, David J.,Newman, Christopher J.,Fleet, George W. J.
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p. 1855 - 1859
(2007/10/03)
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- Pyridine Coenzyme Analogues. 3. Synthesis of Three NAD+ Analogues Containing a 2'-Deoxy-2'-substituted Nicotinamide Arabinofuranosyl Moiety
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A general method for the preparation of 2'-deoxy-2'-substituted arabino-nicotinamide-adenine dinucleotide (NAD) analogues is described.Starting from 1,2:5,6-di-O-isopropylidene-α-D-allofuranose, the 2'-amino-, 2'-azido-, and 2'-fluoro-arabino-NAD analogues have been prepared.We report an improved phosphorylation procedure for nicotinamide nucleosides using pyrophosphoryl chloride in m-cresol.The selective reduction of azido substituents by aqueous dithiothreitol (DTT) in the presence of the readily available nicotinamide moiety is also reported.With both the 2'-azido and the 2'-fluoro substituents the cis configuration predominates for the incoming nicotinamide, thus allowing the steroselective formation of the β anomer in high yield.
- Sleath, Paul R.,Handlon, Anthony L.,Oppenheimer, Norman J.
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p. 3608 - 3613
(2007/10/02)
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- 3,6-DIDEOXY-3,6-IMINO-1,2-O-ISODROPYLIDENE-α-D-GLUCOFURANOSE AS A DIVERGENT INTERMEDIATE FOR THE SYNTHESIS OF HYDROXYLATED PYRROLIDONES: SYNTHESIS IF 1,4-DIDEOXY-1,4-IMINO-L-GULITOL, 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL, 2S,3S,4R,-3,4-DIHYDROXYPROLINE AND (1S,
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An efficient synthesis of the p-toluenesulphonate salt of 3,6-dideoxy-3,6-imino-1,2-O-isopropylidene-α-D-glucofuranose (1) from glucose is reported; the potential of (1) in making hydroxylated pyrrolidines is illustrated by the preparation of 1,4-dideoxy-
- Austin, Geoffrey N.,Baird, Peter D.,Fleet, George W. J.,Peach, Josephine M.,Smith, Paul W.,Watkin, David J.
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p. 3095 - 3108
(2007/10/02)
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- Synthesis of 3-Acetamido- and 3-Azido-3-deoxy-1,2-O-isopropylidene-α-D-xylohexofuran-5-ulose
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The 3-substituted-5,6-ene derivatives (10 and 14), prepared from diacetoneglucose, have been subjected to oxymercuration-demercuration reaction.The resulting 5-hydroxy compounds (11 and 16) have been oxidised to the title compounds (12 and 17).
- Gurjar, M. K.,Patil, V. J.
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p. 1017 - 1020
(2007/10/02)
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- Synthesis of N-Acetyl-(1R,5R)-6-aza-2-oxabicyclooctan-3-one
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A fifteen-step synthesis of N-acetyl-(1R,5R)-6-aza-2-oxabicyclooctan-3-one (Geissman-Waiss lactone), an established chiral precursor for (+)-retronecine, is described starting from D-glucose.
- Gurjar, Mukund K.,Patil, Vijay J.
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p. 1282 - 1283
(2007/10/02)
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- Synthesis and Reactions of 3-O-Phosphoniogluco- and Allofuranoses
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Starting from the bicyclic gluco- (3,5,7, and 9) and allofuranoses 11 the isolable 3-O-phosphoniocarbohydrates (4,6,8,10, and 12) were synthesized by reaction with triphenylphosphane (1), diethyl azodicarboxylate (2), and alkylating or acylating agents.On heating, the various allo configurated salts 12 are converted into the corresponding at C-3 epimeric gluco configurated substitution products offering a wide range of flexibility.The reactions of the gluco configurated salts depend strongly on the type of nucleophile to be introduced and from neighboring groups in t he carbohydrate skeleton.The iodide 4a and the azide 4g react by substitution forming the allo derivatives 15.In contrast, bromide, chloride, and sulfonate as gegen-ions mainly cause rearrangement of the 5,6-isopropylidene bridge or opening of the 5,6-anhydro structure.
- Kunz, Horst,Schmidt, Peter
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p. 1245 - 1260
(2007/10/02)
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