- Regio- And diastereoselective Pd-catalyzed synthesis of C2-aryl glycosides
-
An efficient regio- and diastereoselective arylation method of readily available 2,3-glycals with various aryl iodides has been established. Using the Pd(OAc)2/AsPh3 precatalytic system, this protocol proved to be general to prepare a variety of substituted C2-aryl glycosides in good yields with complete diastereoselectivity.
- Alami, Mouad,Franco, Rémi,Gandon, Vincent,Ghouilem, Juba,Messaoudi, Samir,Retailleau, Pascal
-
supporting information
p. 7175 - 7178
(2020/07/14)
-
- Selective Synthesis of Some Aminosugars via Catalytic Aminohydroxylation of Protected 2,3-Unsaturated d -Gluco- And d -Galacto-2-hexenopyranosides
-
The aminohydroxylation of methyl 4,6-di-O-(tert-butyldimethylsilyl)-2,3-unsaturated α-d-glucopyranoside proceeds in the presence of chloramine-T, OsO4 (4 mol %), (DHQ)2PHAL (5 mol %), and triethylbenzylammonium chloride (TEBAC) in both a stereoselective a
- Fukuhara, Ippei,Matsubara, Ryosuke,Hayashi, Masahiko
-
supporting information
p. 9179 - 9189
(2020/08/14)
-
- Montmorillonite-catalyzed glysosylation of alcohols with glycals derived from galactose and glucose under microwave-induced reactions
-
Montmorillonite K10-catalyzed glycosylation of alcohols with glycals obtained from galactose and glucose is performed efficiently using microwave irradiation with good anomeric selectivity.
- Yadav, Ram Naresh,Banik, Indrani,Banik, Bimal Krishna
-
p. 1385 - 1387
(2020/06/27)
-
- Synthesis of paclitaxel. 1. synthesis of the abc ring of paclitaxel by SmI2-mediated cyclization
-
A convergent synthesis of the ABC ring of antitumor natural product paclitaxel (Taxol) is described. SmI2-mediated reductive cyclization of an allylic benzoate possessing an aldehyde function, synthesized from tri-O-acetyl-d-glucal and 1,3-cyclohexanedione, smoothly afforded the highly strained 6-8-6 tricarbocyclic structure in 66% yield.
- Fukaya, Keisuke,Tanaka, Yuta,Sato, Ayako C.,Kodama, Keisuke,Yamazaki, Hirohisa,Ishimoto, Takeru,Nozaki, Yasuyoshi,Iwaki, Yuki M.,Yuki, Yohei,Umei, Kentaro,Sugai, Tomoya,Yamaguchi, Yu,Watanabe, Ami,Oishi, Takeshi,Sato, Takaaki,Chida, Noritaka
-
supporting information
p. 2570 - 2573
(2015/06/16)
-
- Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)-C(3) Unsaturated and α-d-Mannopyranosyl Sulfones
-
An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and α-d-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access α-d-mannopyranosyl sulfones in good yields with high regioselectivity.
- Chittela, Sravanthi,Reddy, Thurpu Raghavender,Radha Krishna, Palakodety,Kashyap, Sudhir
-
p. 7108 - 7116
(2015/07/28)
-
- Linearization of carbohydrate derived polycyclic frameworks
-
We report easy access to carbohydrate derived diverse tricyclic skeletons which could be beneficial for exploring polyfunctionalized chiral alicycles. The key reaction to assemble a sugar fused tricyclic core is intermolecular tandem esterification and 1,3-dipolar cycloaddition. The framework was elaborated using amide forming reactions, opening of isoxazolidine rings followed by N and O-acylations. The sequences provide distinct, spatially separated and encoded chemical entities that may pave the way to investigate cell functions.
- Singh, Priyanka,Panda, Gautam
-
p. 31892 - 31903
(2014/08/18)
-
- Ferrier rearrangement and 2-deoxy sugar synthesis from d-glycals mediated by layered α-zirconium sulfophenylphosphonate-methanphosphonate as heterogeneous catalyst
-
Layered α-zirconium sulfophenylphosphonate-methanphosphonate is a solid acid catalyst that catalyzes Ferrier rearrangement from d-glycals and alcoholic nucleophiles under mild reaction conditions in short time and good yields. Notably, the combination of α-zirconium sulfophenylphosphonate- methanphosphonate and lithium bromide change the regioselectivity of this process affording 2-deoxy sugars in good yields. Graphical Abstract: [Figure not available: see fulltext.]
- Rosati, Ornelio,Curini, Massimo,Messina, Federica,Marcotullio, Maria Carla,Cravotto, Giancarlo
-
p. 169 - 175
(2013/03/13)
-
- Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions
-
Catalytic amounts of tellurium(IV) tetrachloride were used to promote the O-glycosylation of 3,4,6-tri-O-acetyl-d-glucal to give the corresponding 2,3-unsaturated-O-glycosides. With simple alcohols, the desired compounds were obtained in good yields and excellent anomeric selectivity in a short reaction time using only 2 mol % of the catalyst. The application of the method in the synthesis of a small set of glycopyranosides with rigid or flexible linkers gave the corresponding α anomers as products in good yields. Further applications of some of the synthesized compounds in allylation reaction of aldehydes gave the corresponding homoallylic alcohols in good yields.
- Freitas, Juliano C. R.,Couto, Tulio R.,Paulino, Antonio A. S.,Malvestiti, Ivani,Oliveira, Roberta A.,Menezes, Paulo H.,De Freitas Filho, Joao R.
-
p. 10611 - 10620,10
(2012/12/12)
-
- Stereoselective synthesis of pseudoglycosides catalyzed by TeCl4 under mild conditions
-
Catalytic amounts of tellurium(IV) tetrachloride were used to promote the O-glycosylation of 3,4,6-tri-O-acetyl-d-glucal to give the corresponding 2,3-unsaturated-O-glycosides. With simple alcohols, the desired compounds were obtained in good yields and excellent anomeric selectivity in a short reaction time using only 2 mol % of the catalyst. The application of the method in the synthesis of a small set of glycopyranosides with rigid or flexible linkers gave the corresponding α anomers as products in good yields. Further applications of some of the synthesized compounds in allylation reaction of aldehydes gave the corresponding homoallylic alcohols in good yields.
- Freitas, Juliano C.R.,Couto, Túlio R.,Paulino, Ant?nio A.S.,De Freitas Filho, Jo?o R.,Malvestiti, Ivani,Oliveira, Roberta A.,Menezes, Paulo H.
-
p. 8645 - 8654
(2012/10/29)
-
- Iron(III) triflate, a new efficient catalyst for Type i Ferrier Rearrangement
-
By using iron(III) triflate as catalyst, an improved method for the synthesis of 2,3-unsaturated-O-glycosides has been established. A series of 2,3-unsaturated-O-glucosides were obtained from 2,4,6-tri-O-acetyl-d-glucal in good yield and high anomeric selectivity.
- Chen, Peiran,Wang, Shaoshan
-
supporting information; experimental part
p. 5356 - 5362
(2012/09/07)
-
- Aluminium triflate catalysed O-glycosidation: Temperature-switched selective Ferrier rearrangement or direct addition with alcohols
-
A temperature-controlled mechanism switch between the Al(OTf) 3-catalysed direct addition of alcohols or the Ferrier rearrangement reactions in some glycals is presented. The scope and limitations are investigated as are the influence of the st
- Williams, D. Bradley G.,Simelane, Sandile B.,Kinfe, Henok H.
-
supporting information; experimental part
p. 5636 - 5642
(2012/08/07)
-
- 2,3-Dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercular agents: Design, synthesis, biological evaluation and SAR studies
-
The alarming resurgence of tuberculosis (TB) underlines the urgent need for development of new and potent anti-TB drugs. Towards this goal we herein report the design and synthesis of 2,3-dideoxy hex-2-enopyranosid-4-uloses as promising new anti-tubercula
- Saquib, Mohammad,Husain, Irfan,Sharma, Smriti,Yadav, Garima,Singh, Vipul K.,Sharma, Sandeep K.,Shah, Priyanka,Siddiqi, Mohammad Imran,Kumar, Brijesh,Lal, Jawahar,Jain, Girish K.,Srivastava, Brahm S.,Srivastava, Ranjana,Shaw, Arun K.
-
scheme or table
p. 2217 - 2223
(2011/06/22)
-
- Convertible formation of different glycoside using molecular iodine
-
The observation of convertible formation between 2-deoxy-2-iodo-O- glycosides and 2,3-unsaturated glycoside was described. The selective formation of 2-deoxy-2-iodo-O-glycosides was found from the reaction of D-glucal with iodine in the excess alcohol acceptor or the addition of ceric ammonium nitrate as additive while the addition of a stoichiometric amount of alcohol in solvent favored 2,3-unsaturated glycosides formation. The Japan Institute of Heterocyclic Chemistry.
- Saeeng, Rungnapha,Sirion, Uthaiwan,Sirichan, Yada,Trakulsujaritchok, Thanida,Sahakitpichan, Poolsak
-
experimental part
p. 2569 - 2580
(2011/04/22)
-
- A facile H2SO4/4 ? molecular sieves catalyzed synthesis of 2,3-unsaturated O -glycosides via ferrier-type rearrangement
-
A novel method for synthesizing 2,3-unsaturated glycosides has been developed using a metal-free catalytic system. This catalyst, sulfuric acid/4 molecular sieves can catalyze the reaction of 3,4,6-tri-O-acetyl-d-glucals and a wide range of alcohols at room temperature, affording 2,3-unsaturated glycosides in good -selectivity (α/β> 6:1) via a Ferrier-type rearrangement. Georg Thieme Verlag Stuttgart - New York.
- Zhou, Jiafen,Zhang, Bo,Yang, Guofang,Chen, Xuan,Wang, Qingbing,Wang, Zhongfu,Zhang, Jianbo,Tang, Jie
-
experimental part
p. 893 - 896
(2010/07/16)
-
- H2SO4-SiO2: Highly efficient and novel catalyst for the Ferrier-type glycosylation
-
Sulfuric acid immobilized on silica gel is designed as a very useful catalyst for synthesis of 2,3-unsaturated glycopyranosides. This handy, metal-free, environment friendly transformation provides high yields and α-stereoselectivities in a very few amount (0.02 eq.) of catalyst and in short reaction times (10 min).
- Zhou, Jia Fen,Chen, Xuan,Wang, Qing Bing,Zhang, Bo,Zhang, Li Yan,Yusulf, Abdullh,Wang, Zhong Fu,Zhang, Jian Bo,Tang, Jie
-
experimental part
p. 922 - 926
(2011/11/12)
-
- ZnCl2/alumina impregnation catalyzed Ferrier rearrangement: an expedient synthesis of pseudoglycosides
-
An improved method for the synthesis of 2,3-unsaturated-O-glycosides has been developed. ZnCl2 impregnated on activated alumina acts as an excellent reagent system for the conversion of 2,4,6-tri-O-acetyl-d-glucal to 2,3-unsaturated-O-glycosides with high α-selectivity.
- Gorityala, Bala Kishan,Lorpitthaya, Rujee,Bai, Yaguang,Liu, Xue-Wei
-
experimental part
p. 5844 - 5848
(2009/12/01)
-
- Synthesis of 2,3-unsaturated O- and N-glycosides by HBF4· SiO2-catalyzed ferrier rearrangement of D-glycals
-
Fluoroboronic acid adsorbed on silica gel (HBF4·SiO 2) catalyzes the Ferrier rearrangement of per-O-acetylated glycals with alcohols and sulfonamides to give 2,3-unsaturated O- and N-glycosides in good to excellent yield and with high α-stereoselectivity. Georg Thieme Verlag Stuttgart.
- Rodríguez, Oscar Mariano,Colinas, Pedro Alfonso,Bravo, Rodolfo Daniel
-
scheme or table
p. 1154 - 1156
(2009/10/17)
-
- Kinetically controlled Ferrier rearrangement of 3-O-mesyl-d-glycal derivatives
-
The Ferrier rearrangement, which is widely used in carbohydrate chemistry, is generally performed under acidic conditions to give an α anomer with high stereoselectivity. We have found that 3-O-mesyl-d-glycals 2-4 were smoothly reacted with alcohols in th
- Watanabe, Yuhya,Itoh, Tsubasa,Sakakibara, Tohru
-
experimental part
p. 516 - 520
(2009/05/11)
-
- Indium trichloride promoted stereoselective synthesis of O-glycosides from trialkyl orthoformates
-
A novel, highly stereoselective method for O-glycosylation of glycals and glycosylbromides is developed using orthoformates as acceptors in the presence of InCl3 to afford the corresponding O-glycopyranosides in 66-94% yield. Both perbenzyl and peracetyl glycals afford the corresponding 2,3-unsaturated-O-glycosides with high α-selectivity. Stoichiometric amounts of orthoformates are sufficient to bring about this transformation instead of large excesses of alcohols.
- Mukherjee, Debaraj,Yousuf, Syed Khalid,Taneja, Subhash C.
-
p. 4944 - 4948
(2008/09/21)
-
- Synthesis of 2,3-unsaturated glycosides via metal-free Ferrier reaction
-
Hexafluoroisopropanol (HFIP) is explored as an effective medium for the synthesis of 2,3-unsaturated glycosides through allylic rearrangement of 3,4,6-tri-O-acetyl glucal. This metal-free, exclusively solvent-promoted Ferrier glycosylation, affords products in good to excellent yields and with good α-selectivity.
- De, Kavita,Legros, Julien,Crousse, Benoit,Bonnet-Delpon, Danièle
-
p. 10497 - 10500
(2008/12/23)
-
- Design of chiral auxiliaries for the allene ether Nazarov cyclization
-
A 1,3- or a 1,4-cis axial tert-butyldimethylsilyloxy substituent on the pyranose derived chiral auxiliary for the allene ether Nazarov cyclization leads to products in high optical purity. α-Pyranose and β-pyranose derived auxiliaries lead to enantiomeric products. Copyright
- Banaag, April R.,Tius, Marcus A.
-
p. 5328 - 5329
(2008/02/04)
-
- Diastereoselective synthesis of 2′,3′-dideoxy- β-C- glucopyranosides as intermediates for the synthesis of 2′,3′- dideoxy-β-D-glucopyranosyl-C-nucleosides
-
An extension of the Vorbrueggen method of nucleotide synthesis for the synthesis of C-glucopyranosides, as intermediates for C-nucleosides, is described. It could be shown that the diastereoselectivity of the reaction can be tuned by a simple change of protecting groups. Copyright Taylor & Francis Group, LLC.
- Loepfe, Michael,Siegel, Jay S.
-
p. 1029 - 1035
(2008/09/17)
-
- Novel approach towards C-C-linked carbohydrate dimers via Claisen rearrangement of a disaccharide allyl ketene acetal
-
A disaccharide derivative was synthesised by coupling tri-O-benzyl-D-glucal with an allylic sugar alcohol in a glycosyloxyselenation reaction. Subsequent oxidation followed by syn-elimination of the selenoxide and in situ rearrangement of the inter-mediat
- Juers, Stefan,Thiem, Joachim
-
p. 2117 - 2120
(2008/02/03)
-
- TRANSACETALISATION PROCESS
-
The invention relates to the resolution of racemic mixtures, and in particular to the separation of enantiomers of chiral alcohols utilising recyclable chiral auxiliaries. The present invention also relates to a process for preparing these recyclable chiral auxiliaries using an enantiomerically pure alcohol.
- -
-
Page/Page column 41-42
(2010/02/13)
-
- Bi(OTf)3 and SiO2-Bi(OTf)3 as effective catalysts for the ferrier rearrangement
-
Bi(OTf)3 and SiO2-Bi(OTf)3 are found to effectively catalyze the Ferrier rearrangement of tri-O-acetyl glycals with different alcohols providing an effective route to 2,3-imsaturated O-glycosides with good anomeric selectivity and good to excellent yields after short reaction times.
- Lokesh Babu,Khare, Anakshi,Vankar, Yashwant D.
-
p. 884 - 892
(2007/10/03)
-
- A mild, efficient and α-selective glycosidation by using potassium dodecatungstocobaltate trihydrate as catalyst
-
Treatment of tri-O-acetyl-D-glucal3,4,6-Tri-O-acetyl-1,5-anhyro-2-deoxy-D- arabinahex-1-enitol.1 1 with several alcohols in the presence of catalytic amount of POM (K5CoW12O40· 3H2O) as a heterogeneous, reusable, efficient and environmentally benign catalyst under neutral conditions and ambient temperature gave the corresponding 2,3-unsaturated glycopyranosides in excellent yields, with good anomeric selectivity. This catalyst proved to be not efficient for phenols.
- Rafiee, Ezzat,Tangestaninejad, Shahram,Habibi, Mohammad H.,Mirkhani, Valiollah
-
p. 3611 - 3614
(2007/10/03)
-
- Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals
-
Perchloric acid supported on silica gel acts as an excellent reagent system in converting glucals into 2,3-unsaturated-O-glucosides in good to excellent yields in short reaction time with good α selectivity. Primary, secondary, and allylic alcohols, phenols, and thiols react with 3,4,6-tri-O-acetyl glucal with equal ease. In addition to this, a chiral furan diol is obtained from unprotected D-glucal or D-galactal in good yields.
- Agarwal, Aditi,Rani, Shikha,Vankar, Yashwant D.
-
p. 6137 - 6140
(2007/10/03)
-
- Total synthesis of Brevetoxin-B
-
Brevetoxin-B (BTX-B), produced by the red tide organism, Gymnodium breve Davis, is the first member of marine polycyclic ethers to be structurally elucidated and one of the most potent neurotoxins. The structural feature is a trans-fused polycyclic ether
- Matsuo, Goh,Kawamura, Koji,Hori, Nobuyuki,Matsukura, Hiroko,Nakata, Tadashi
-
p. 14374 - 14376
(2007/10/03)
-
- A new bismuth nitrate-induced stereospecific glycosylation of alcohols
-
Bismuth nitrate-catalyzed stereospecific glycosylation of alcohol with glycal has been developed.
- Banik, Bimal K.,Adler, Dorothy,Nguyen, Phuong,Srivastava, Neeta
-
p. 101 - 104
(2007/10/03)
-
- Highly Deoxygenated Sugars. II. Synthesis of Chiral Cyclopentenes via Novel Carbocyclization of C-4 Branched Deoxysugars
-
Tri-O-acetyl-D-glucal (1) was converted via Ferrier type II rearrangement with high α-selectivity to 2,3-unsaturated methyl glycosides 2a and 2b using ferric chloride as the catalyst. Palladium induced allylic substitution with sodium tert-butylacetoacetate as a nucleophile leads to C-4 branched sugars. Subsequent hydrogenation followed by treatment with trifluoroacetic acid affords the highly functionalized chiral cyclopentene derivative 5a as a versatile chiral building block for cyclopentanoids.
- Krohn, Karsten,Gehle, Dietmar,Kamp, Oliver,Van Ree, Teunis
-
p. 377 - 383
(2007/10/03)
-
- Synthesis of C7-C16-alkyl 2,3-dideoxy glucosides from glucose and fatty alcohols
-
C7-C16-alkyl 2,3-dideoxy glucosides have been synthesized from glucose and C7-C16-alkanols by Ferrier reaction using boron trifluoride etherate (BF3·Et2O) as Lewis acid catalyst in key step.
- Konstantinovic,Predojevic,Gojkovic,Ratkovic,Mojsilovic,Pavlovic
-
p. 1242 - 1244
(2007/10/03)
-
- Indium trichloride catalyzed glycosidation. An expeditious synthesis of 2,3-unsaturated glycopyranosides
-
Treatment of tri-O-acetyl-D-glucal 1 with various alcohols and phenols in the presence of InCl3/CH2Cl2 at ambient temperature gave the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides in excellent yields with short reaction times and good anomeric selectivity. (C) 2000 Elsevier Science Ltd.
- Sobhana Babu, Boga,Kuppuswamy Balasubramanian, Kalpattu
-
p. 1271 - 1274
(2007/10/03)
-
- Synthesis of amino-sugars using the directed dihydroxylation reaction
-
The synthesis of protected forms of two amino-sugars, talosamine 1 and allosamine 2, is described; the syn, syn stereochemistry at C-2, C-3 and C-4 was controlled by the use of a hydrogen-bonding directed dihydroxylation reaction using stoichiometric and catalytic OsO4; proof of the relative stereochemistry of the allosamine series was obtained through an X-ray crystal structure of a protected derivative.
- Donohoe, Timothy J.,Blades, Kevin,Helliwell, Madeleine
-
p. 1733 - 1734
(2007/10/03)
-
- Lithium tetrafluoborate catalyzed ferrier rearrangement - Facile synthesis of alkyl 2,3-unsaturated glycopyranosides
-
Treatment of tri-O acetyl-D-galactal 1 and tri-O-acetyl-D-glucal 2 with diverse alcohols in the presence of LiBF4 in CH3CN, furnished alkyl, 2,3- unsaturated glycopyranosides 3-18 (50-86%).
- Sobhana Babu,Balasubramanian
-
p. 4299 - 4305
(2007/10/03)
-
- Simple Designs for the Construction of Complex Trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations
-
A successful design for the construction of trans-fused medium-size cyclic ethers is described.The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps.The general approach involves the intramolecular addition of a stable γ-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system.While the present strategy was mostly developed around racemic models, the potential for adoption of enantioselective features is immediate.The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.
- Alvarez, Eleuterio,Diaz, Maria T.,Perez, Ricardo,Ravelo, Jose L.,Regueiro, Alicia,et al.
-
p. 2848 - 2876
(2007/10/02)
-
- 110. Warum Pentose- und nicht Hexose-Nucleinsaeuren? (Teil II) Oligonucleotide aus 2',3'-Dideoxy-β-D-glucopyranosyl-Bausteinen ('Homo-DNS'): Herstellung - Why Pentose and Not Hexose Nucleic Acids? Part II. Preparation of Oligonucleotides Containing 2',3'-
-
This paper describes the preparation of the 2',3'-dideoxy-β-D-glucopyranosyl-(= 2',3'-dideoxy-β-D-erythro-hexapyranosyl)-derived nucleosides of the five bases adenine, cytosine, guanine, thymine, and uracil (= 'homo-deoxyribonucleosides') as well as the s
- Boehringer, Markus,Roth, Hans-Joerg,Hunziker, Juerg,Goebel, Michael,Krishnan, Ravichandran,et al.
-
p. 1416 - 1477
(2007/10/02)
-
- Model studies directed towards microalgal polyether toxins. Use of 2-phenyl-sulphonyl cyclic ethers in the preparation of trans, syn, trns α-alkyl,β-hydroxy-substituted tetrahydropyran subunits
-
A synthesis of optically active C7- and C8-tetrahydropyranyl subunits with suitable functionalities for further elaboration of transfused polyether toxins was achieved from glucal acetate via the use of 2-phenylsulphonyl intermediate
- Alvarez,Rico,Rodriguez,Zurita,Martin
-
p. 3385 - 3388
(2007/10/02)
-
- The facile conversion of pyranoid glycals into 2-deoxy-glycosidic orthoesters
-
The formation of 2-deoxy-glycosidic orthoesters involving the palladium(II) catalysed reaction of pyranoid glycals with alcohols in the presence of sodium hydrogen carbonate is described.
- Holzapfel, Cedric W.,Engelbrecht, Gerhardus J.,Verdoorn, Gerhard H.
-
p. 433 - 444
(2007/10/02)
-
- SYNTHESIS AND STEREOCHEMICAL CHARACTERIZATION OF OPTICALLY ACTIVE 2-METHOXY-3,4-DIHYDRO-2H-PYRAN
-
Samples of (+)-2-methoxy-3,4-dihydro-2H-pyran (1) have been prepared starting from methyl α-D-glucopyranoside and from tri-O-acetyl-D-glucal; the absolute configuration as well as the maximum rotatory power of 1 have been established.
- Menicagli, Rita,Malanga, Corrado,Pecunioso, Angelo,Lardicci, Luciano
-
-
- Vers la synthese totale de la d,l-desosamine. Formation du carbon anomere au moyen de PhSeBr
-
Reaction of phenylselenyl bromide with dihydropyrans in the presence of methanol, followed by oxidative elimination, leads to α,β-unsaturated acetals.This method, which constitutes a new way for generating an anomeric center in the total synthesis of hexopyranose derivatives, has been applied towards the synthesis of methyl 3,4,6-trideoxy-3-dimethylamino-D,L-xylo hexopyranoside (methyl D,L-desosamide).
- Berube, Gervais,Luce, Eric,Jankowski, Krzysztof
-
p. 109 - 111
(2007/10/02)
-
- PALLADIUM-ASSISTED CARBOHYDRATE REACTIONS I. SODIUM CYANOBOROHYDRIDE-PROMOTED ALLYLIC REARRANGEMENTS OF C-6 SUBSTITUTED PYRANOSIDE GLYCALS.
-
Methoxypalladation of C-6 substituted pyranoside glycals followed by addition of sodium cyanoborohydride gives allylic rearrangement products in good yield with excellent regio- and stereoselectivity.
- Dunkerton, Lois V.,Brady, Kevin T.,Mohamed, Farhana
-
p. 599 - 602
(2007/10/02)
-