- Mechanism of the reductive cleavage reaction of permethylated methyl D-glycopyranosides
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The mechanism of the reductive cleavage reaction of permethylated methyl D-glycopyranosides was investigated by measuring the rate of reaction. Glycosides employed were of α-Glc, β-Glc, α-Man, α-Gal, and β-Gal. Seven silanes were used to explore the reactivities of the reducing agents as well as to examine the stereoelectronic effects of the agents. Trimethylsilyl trifluoromethanesulfonate was employed as catalyst. In general, the rates of β anomers were about twice as fast as those of the α anomers. The rates of anomerization were about five to ten times lower than those of reduction. A cyclic oxonium ion has been proposed as a sole intermediate for the reductive cleavage of the α-glycoside linkage, but the attack of the reducing agent on both cyclic and acyclic forms as well as on the substrate-Lewis acid complex seems to be involved for the β anomer. Copyright (C) 1999 Elsevier Science Ltd.
- Lee, Chang Kiu,Kim, Eun Ju
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- A "traceless" Directing Group Enables Catalytic SN2 Glycosylation toward 1,2- cis-Glycopyranosides
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Generally applicable and stereoselective formation of 1,2-cis-glycopyranosidic linkage remains a long sought after yet unmet goal in carbohydrate chemistry. This work advances a strategy to this challenge via stereoinversion at the anomeric position of 1,2-trans glycosyl ester donors. This SN2 glycosylation is enabled under gold catalysis by an oxazole-based directing group optimally tethered to a leaving group and achieved under mild catalytic conditions, in mostly excellent yields, and with good to outstanding selectivities. The strategy is also applied to the synthesis of oligosaccharides.
- Fu, Yue,Liu, Peng,Ma, Xu,Zhang, Liming,Zheng, Zhitong,Zhu, Xijun
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p. 11908 - 11913
(2021/08/20)
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- Glucosylpolyphenols as Inhibitors of Aβ-Induced Fyn Kinase Activation and Tau Phosphorylation: Synthesis, Membrane Permeability, and Exploratory Target Assessment within the Scope of Type 2 Diabetes and Alzheimer's Disease
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Despite the rapidly increasing number of patients suffering from type 2 diabetes, Alzheimer's disease, and diabetes-induced dementia, there are no disease-modifying therapies that are able to prevent or block disease progress. In this work, we investigate the potential of nature-inspired glucosylpolyphenols against relevant targets, including islet amyloid polypeptide, glucosidases, and cholinesterases. Moreover, with the premise of Fyn kinase as a paradigm-shifting target in Alzheimer's drug discovery, we explore glucosylpolyphenols as blockers of Aβ-induced Fyn kinase activation while looking into downstream effects leading to Tau hyperphosphorylation. Several compounds inhibit Aβ-induced Fyn kinase activation and decrease pTau levels at 10 μM concentration, particularly the per-O-methylated glucosylacetophloroglucinol and the 4-glucosylcatechol dibenzoate, the latter inhibiting also butyrylcholinesterase and β-glucosidase. Both compounds are nontoxic with ideal pharmacokinetic properties for further development. This work ultimately highlights the multitarget nature, fine structural tuning capacity, and valuable therapeutic significance of glucosylpolyphenols in the context of these metabolic and neurodegenerative disorders.
- De Matos, Ana M.,Blázquez-Sánchez, M. Teresa,Bento-Oliveira, Andreia,De Almeida, Rodrigo F. M.,Nunes, Rafael,Lopes, Pedro E. M.,MacHuqueiro, Miguel,Cristóv?o, Joana S.,Gomes, Cláudio M.,Souza, Cleide S.,El Idrissi, Imane G.,Colabufo, Nicola A.,Diniz, Ana,Marcelo, Filipa,Oliveira, M. Concei??o,López, óscar,Fernandez-Bola?os, José G.,D?twyler, Philipp,Ernst, Beat,Ning, Ke,Garwood, Claire,Chen, Beining,Rauter, Amélia P.
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p. 11663 - 11690
(2020/11/26)
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- Establishment of Guidelines for the Control of Glycosylation Reactions and Intermediates by Quantitative Assessment of Reactivity
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Stereocontrolled chemical glycosylation remains a major challenge despite vast efforts reported over many decades and so far still mainly relies on trial and error. Now it is shown that the relative reactivity value (RRV) of thioglycosides is an indicator for revealing stereoselectivities according to four types of acceptors. Mechanistic studies show that the reaction is dominated by two distinct intermediates: glycosyl triflates and glycosyl halides from N-halosuccinimide (NXS)/TfOH. The formation of glycosyl halide is highly correlated with the production of α-glycoside. These findings enable glycosylation reactions to be foreseen by using RRVs as an α/β-selectivity indicator and guidelines and rules to be developed for stereocontrolled glycosylation.
- Chang, Chun-Wei,Wu, Chia-Hui,Lin, Mei-Huei,Liao, Pin-Hsuan,Chang, Chun-Chi,Chuang, Hsiao-Han,Lin, Su-Ching,Lam, Sarah,Verma, Ved Prakash,Hsu, Chao-Ping,Wang, Cheng-Chung
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supporting information
p. 16775 - 16779
(2019/11/03)
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- Structural analysis of novel kestose isomers isolated from sugar beet molasses
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Eight kestose isomers were isolated from sugar beet molasses by carbon-Celite column chromatography and HPLC. GC-FID and GC-MS analyses of methyl derivatives, MALD-TOF-MS measurements and NMR spectra were used to confirm the structural characteristics of the isomers. The 1H and 13C NMR signals of each isomer saccharide were assigned using COSY, E-HSQC, HSQC-TOCSY, HMBC and H2BC techniques. These kestose isomers were identified as α-D-fructofuranosyl-(2-> 2)-α-D-glucopyranosyl-(1 2)-β-D-fructofuranoside, α-D-fructofuranosyl-(2-> 3)-β-D-fructofuranosyl-(2 1)-α-D-glucopyranoside, α-D-fructofuranosyl-(2-> 4)-β-D-fructofuranosyl-(2 1)-α-D-glucopyranoside, β-D-fructofuranosyl-(2- > 4)-β-D-fructofuranosyl-(2 1)-α-D-glucopyranoside, β-D-fructofuranosyl-(2- > 3)-α-D-glucopyranosyl-(1 2)-β-D-fructofuranoside, α-D-fructofuranosyl-(2- > 1)-β-D-fructofuranosyl-(2 1)-α-D-glucopyranoside, α-D-fructofuranosyl-(2- > 6)-α-D-glucopyranosyl-(1 2)-β-D-fructofuranoside, and α-D-fructofuranosyl-(2- > 6)-β-D-fructofuranosyl-(2 1)-α-D-glucopyranoside. The former five compounds are novel saccharides.
- Shiomi, Norio,Abe, Tatsuya,Kikuchi, Hiroto,Aritsuka, Tsutomu,Takata, Yusuke,Fukushi, Eri,Fukushi, Yukiharu,Kawabata, Jun,Ueno, Keiji,Onodera, Shuichi
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- Conversion of β-glycopyranoside to α-glycopyranoside by photo-activated radical reaction
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By using carbon tetrachloride as the chloride radical and boron trifluoride etherate as the Lewis acid, the halogen-light-activated anomeric inversion of glycoside was achieved. This reaction is a novel guide to invert the glycosidic bond from a β-anomer to an α-anomer.
- Lai, Yu-Chen,Luo, Chin-Hung,Chou, Hsin-Chun,Yang, Cheng-Jhang,Lu, Le,Chen, Chien-Sheng
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supporting information
p. 2474 - 2477
(2016/05/24)
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- Visible light mediated activation and O-glycosylation of thioglycosides
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Visible light catalysis allows the efficient construction of single electron transfer (SET) redox cycles that result in minimal formation of byproducts and proceed under exogenous control of a removable light source. The O-glycosylation of thioglycosides via visible light photoredox chemistry is reported. Mechanistic studies show that the reaction is fully light responsive and support a mechanism involving decomposition of an oxidatively generated sulfur radical cation and propagation via reduction of the thiol side product.
- Wever, Walter J.,Cinelli, Maris A.,Bowers, Albert A.
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supporting information
p. 30 - 33
(2013/03/28)
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- New method for regioselective glycosylation employing saccharide oxyanions
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As an alternative concept for glycosylation, the prior activation of acceptor hydroxy groups for selective glycosidic bond formation, was investigated to give complex oligosaccharides. Oxyanions obtained from partially protected saccharides were glycosylated by employing glycopyranosyl halides, and the regiochemical results were studied. Initially, partially methylated methyl-α-D-glucopyranosides were used as a model system to study the underlying mechanistic principles of base-promoted glycosylation. High regioselectivities and stereospecific glycosidic bond formations were achieved, and the scope of the methodology was extended with different perbenzylated glycosyl donors.
- Matwiejuk, Martin,Thiem, Joachim
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experimental part
p. 5860 - 5878
(2011/11/06)
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- Anodic coupling reactions and the synthesis of C-glycosides
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A convenient, two-step procedure has been developed for converting sugar derivatives into C-glycosides containing a masked aldehyde functional group. The chemistry takes advantage of an anodic coupling reaction between an electron-rich olefin and an alcohol. The sequence works for the formation of both furanose and pyranose derivatives if less polarized vinyl sulfide derived radical cation intermediates are used. With more polarized enol ether derived radical cations, the cyclizations work best for the formation of furanose derivatives where the rate of five-membered ring formation precludes elimination reactions triggered by the radical cation.
- Xu, Guoxi,Moeller, Kevin D.
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supporting information; scheme or table
p. 2590 - 2593
(2010/08/22)
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- Selective cleavage of methoxy protecting groups in carbohydrates
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The selective cleavage of methoxy protecting groups next to hydroxy groups is achieved using a radical hydrogen abstraction reaction as the key step. Under the reaction conditions, the hydroxy group generates an alkoxyl radical that reacts with the sterically accessible adjacent methoxy group, which is transformed into an acetal. In the second step, the acetals are hydrolyzed to give alcohols or diols. A one-pot hydrogen abstraction-hydrolysis procedure was also developed. Good yields were usually achieved, and the mild conditions of this methodology were compatible with different functional groups and sensitive substrates such as carbohydrates.
- Boto, Alicia,Hernandez, Dacil,Hernandez, Rosendo,Suarez, Ernesto
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p. 1938 - 1948
(2007/10/03)
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- Efficient and selective removal of methoxy protecting groups in carbohydrates
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(Chemical Equation Presented) The selective removal from carbohydrate substrates of methoxy protecting groups next to hydroxy groups is reported. On treatment with Phl(OAc)2-I2, the methoxy group is transformed into an easily removable acetal. The mild conditions of this methodology are compatible with many functional groups, and good to excellent yields are usually achieved.
- Boto, Alicia,Hernandez, Dacil,Hernandez, Rosendo,Suarez, Ernesto
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p. 3785 - 3788
(2007/10/03)
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- Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry
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(Chemical Equation Presented) Alkoxycarbenium ions have been generated and accumulated as "cation pools" by the low-temperature electrochemical oxidation of α-phenylthioethers. Although an unsuccessful attempt to accumulate glycosyl cations was made, a one-pot method for electrochemical glycosylation, which involves anodic oxidation of thioglycosides to generate glycosyl cation equivalents followed by their reactions with glycosyl acceptors, has been developed.
- Suzuki, Shinkiti,Matsumoto, Kouichi,Kawamura, Kohsuke,Suga, Seiji,Yoshida, Jun-Ichi
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p. 3755 - 3758
(2007/10/03)
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- Mechanism of anomerization of permethylated methyl D-glycopyranosides by trimethylsilyl trifluoromethanesulfonate
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Anomerization of permethylated methyl D-glycopyranosides catalyzed by trimethylsilyl trifluoromethanesulfonate was examined by NMR spectroscopy and gas-liquid chromatography. The initial-rate analysis showed that the rates of anomerization of β to α were faster than those of the opposite at various concentrations of the catalyst. The overall rates of disappearance of the substrates were faster than the rates of appearance of the opposite anomers because of the formation of a pyrylium-type of compound. The structure of the latter was proposed based on 1H and 13C NMR spectra, although it was not isolable. Both cyclic and acyclic oxonium ions appear to be intermediates in the anomerization. The former seems to be the key intermediate for the formation of the pyrylium-type of compound as well as the anomerization of α-glycosidic linkages. β-Glycosidic linkages, on the other hand, appear to undergo anomerization mostly via acyclic oxonium ions.
- Lee, Chang Kiu,Kim, Eun Ju,Lee, In-Sook Han
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p. 243 - 250
(2007/10/03)
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- Peralkylation of Saccharides under Aqueous Conditions
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Treatment of saccharides with sodium hydroxide and alkyl halides in aqueous dimethyl sulfoxide solution offers a very efficient method for the complete alkylation of saccharides in high yields.
- Wang, Hui,Sun, Lihong,Glazebnik, Serge,Zhao, Kang
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p. 2953 - 2956
(2007/10/02)
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- Anomerization and transglycosylation reactions of permethylated methyl D-glycopyranosides
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The anomerization reactions of permethylated methyl D-glycopyranosides in the presence of various Lewis acid catalysts, such as Me3SiOTf, Me3SiOMs, BF3 · OEt2, or TiCl4 were examined in dichloromethane solution. β Anomers of the glycosides anomerized to the α anomer very rapidly, but the anomerizations in the opposite direction were slower. Transglycosylation reactions of the glycosides in the presence of similar catalysts and ethanol gave preferably the α anomers with most substrates employed. No anomerization was observed in the case of the α-mannoside, probably because the α anomer is strongly favored at equilibrium. Nevertheless, transglycosylation took place. The anomerization reactions of permethylated methyl D-glycopyranosides in the presence of various Lewis acid catalysts, such as Me3SiOTf, Me3SiOMs, BF3·OEt2, or TiCl4 were examined in dichloromethane solution. β Anomers of the glycosides anomerized to the α anomer very rapidly, but the anomerization in the opposite direction were slower. Transglycosylation reactions of the glycosides in the presence of similar catalysts and ethanol gave preferably the α anomers with most substrates employed. No amerization was observed in the case of the α-mannoside, probably because the α anomer is strongly favored at equilibrium. Nevertheless, transglycosylation took place.
- Lee,Kim,Lee
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p. 197 - 206
(2007/10/02)
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- 1:1 Adduct Ion Formation of Permethylated Monosaccharides with Organic Cations in FAB Mass Spectrometry
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The 1:1 adduct ion formation between a series of permethylated monosaccharides (M; Ia-Ih) and an organic or a metallic cation (A+) has been examined in quantitative FAB mass spectrometry.In a careful camparison under the same FABMS conditions, the relative (M+A)+ peak intensities increase in the following order of the monosaccharides, and further increase at nearly the same extents in spite of using three different cations such as octylammonium, (methoxycarbonyl)methylammonium, and potassium ions: β-Glc α-Glc α-Gal β-Gal /= α-Man β-Man α-Tal β-Tal.The order and cation-independency clearly indicate the OCH3 configurational effects of M on (M+A)+ adduct ion formation.The findings can be interpreted in terms of multisite electrostatic interaction of oxygens with the cation.Coupled with the results of gas-phase behavior by FABMS/MS(CAD), solution behavior by 1H NMR, and model calculations by MNDO, the characteristic structure of the 1:1 adduct ion is deduced as host-guest type association between permethylated monosaccharides and cationic species in particular cases, at least β-Tal and α-Tal cases.
- Sawada, Masami,Ouyang, Li,Takai, Yoshio,Yamada, Hitoshi,Shizuma, Motohiro,et al.
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p. 1243 - 1252
(2007/10/02)
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- PHOTOINDUCED GENERATION OF GLYCOSYL CATIONS FROM THIOGLYCOSIDES
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Photochemically induced cleavage of thioaryl β-D-glucopyranosides using 1,4-dicyanonaphthalene as an electron-transfer agent, produces glycosyl cations potentially useful in glycosylation reactions.
- Griffin, Gary W.,Bandara, Nayanie C.,Clarke, Margaret A.,Tsang, Wing-Sum,Garegg, Per J.,et al.
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p. 939 - 947
(2007/10/02)
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- Sarasinoside A1: A Saponin Containing Amino Sugars Isolated from a Sponge
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A new saponin designated sarasinoside A1, 1, has been isolated from a sponge, Asteropus sp., collected from Guam Island and also from Truk Lagoon.Acid hydrolysis of sarasinoside A1 afforded the aglycon 2, identified as 3β-hydroxy-4,4-dimethylcholesta-8,24-dien-23-one by spectral analysis.Methanolysis of 1 yielded the methyl glycosides of xylose, glucose, N-acetyl-2-amino-2-deoxygalactose, and N-acetyl-2-amino-2-deoxyglucose.Glycosidic connections were established by a combination of chemical degradations and spectroscopic methods. 1H and 13C NMR assignments were made with the aid of 1H/13C NMR correlations, relayed coherence transfer, and ROESY experiments.This appears to be the first saponin isolated from a sponge.
- Schmitz, Francis J.,Ksebati, Mohamad B.,Gunasekera, Sarath P.,Agarwal, Santosh
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p. 5941 - 5947
(2007/10/02)
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- A new catalyst for reductive cleavage of methylated glycans.
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Several per-O-methylated D-glucans and D-fructans were used as models in an attempt to identify new catalysts for carrying out reductive cleavage. Included in these model studies were several D-glucans that contained 4-linked D-glucopyranosyl residues as well as one having a 4-linked D-glucitol residue, as both types of residue had previously been found to give rise to substantial proportions of artifactual products. These studies led to the development of a new catalyst for carrying out reductive cleavage, namely, a mixture of 5 equivalents of trimethylsilyl methanesulfonate (Me3SiOSO2Me) and 1 equivalent of boron trifluoride etherate (BF3 . Et2O) per equivalent of acetal. This new catalyst was found to accomplish the reductive cleavage of per-O-methylated, 4-linked D-glucopyranosyl residues and 4-linked D-glucitol residues, to give only the expected derivatives of 1,5-anhydro-D-glucitol and D-glucitol, respectively. The mixture of Me3SiOSO2Me and BF3 . Et2O also catalyzed reductive cleavage of the D-fructofuranosyl residues of per-O-methylated sucrose and inulin, to give only the expected derivatives of 2,5-anhydro-D-mannitol and 2,5-anhydro-D-glucitol. Indeed, when used alone, Me3SiOSO2Me also rapidly catalyzed the reductive cleavage of D-fructofuranosyl residues, but, under the same conditions, D-glucopyranosyl residues were unaffected. The results of these and other model studies demonstrated that catalysis of reductive cleavage by the mixture of Me3SiOSO2Me and BF3 . Et2O occurs in a synergistic manner. Examination of the mixture of Me3SiOSO2Me and BF3 . Et2O by 1H-n.m.r. spectroscopy demonstrated that a reaction occurs to generate trimethylsily fluoride and species of the type F2BOSO2Me, FB(OSO2Me)2, or B(OSO2Me)3 via ligand exchange.
- Jun,Gray
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p. 247 - 261
(2007/10/02)
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- METHYLATION OF METHYL α-D-HEXOPYRANOSIDES WITH DIAZOMETHANE IN THE PRESENCE OF A SMALL AMOUNT OF WATER
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The long-time reaction of methyl α-D-gluco-, α-D-manno-, and α-D-galactopyranosides with excess diazomethane-diethyl ether at 25 deg C the presence of water gave all partially methylated methyl α-D-hexopyranosides which differ in number and position of methyl substitution.The presence electrolytes, such as potassium or sodium phosphate, in the reaction medium enhanced the degree of methylation, resulting in preferential formation of tri-O-methyl derivatives of methyl α-D-hexopyranosides.
- Inoue, Yuko,Nagasawa, Kinzo
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p. 181 - 190
(2007/10/02)
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- A FUROSTANOL GLUCURONIDE FROM SOLANUM LYRATUM
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A new furostanol glucuronide and three known glycosides, SL-0, aspidistrin and methyl proto-aspidistrin, were isolated from the fresh immature berries of Solanum lyratum.The structure of the new compound was characterized as 26-O-β-D-glucopyranosyl-(22ξ,25R)-3β,22,26-trihydroxyfurost-5-ene 3-O-α-L-rhamnopyranosyl-(1 -> 2)- 3)>-β-D-glucopyranoside. Key Word Index - Solanum lyratum; Solanaceae; furostanol glucuronide.-24β-ethyl-5α-cholesta-7,trans-22,25(27)-trien-3β-ol; spinasteryl-β-D-glucopyranoside.
- Yahara, Shoji,Murakami, Naomi,Yamasaki, Masaki,Hamada, Toshiyuki,Kinjo, Jun-ei,Nohara, Toshihiro
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p. 2748 - 2750
(2007/10/02)
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- A SIMPLE AND RAPID METHOD FOR THE PERMETHYLATION OF CARBOHYDRATES
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As a result of a study of the permethylation of sugars in such dipolar aprotic solvents as methyl sulphoxide, the hitherto accepted role of the CH3SOCH2- anion is questioned.The HO- and H+ ions appear to be the effective basic agents in these methylation reactions.This conclusion suggested a new method for the permethylation of sugars involving methyl iodide, a solid base (NaOH, KOH, or tert-BuOH/NaOH), and methyl sulphoxide.Excellent yields (98 +/- 2 percent) of permethylation products were obtained in a remarkably short (6-7 min) reaction time.The non-sugar peaks that appear in gas chromatograms of the products of Hakomori methylation were absent when the new reagent was used.
- Ciucanu, Ionel,Kerek, Francisc
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p. 209 - 218
(2007/10/02)
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- Five Steroidal Components from the Rhizomes of Polygonatum odoratum var. pluriflorum
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Five steroidal components (PO-a(1)-PO-e(5)) were obtained from the methanolic extract or its partial hydrolysate of the fresh rhizomes of Polygonatum odoratum var.Pluriflorum, and their chemical structures were characterized as (25 R and S)-spirost-5-en-3β,14α-diol, 3-O-β-D-glucopyranosyl-(1->2)-3)>-β-D-glucopyranosyl-(1->4)-β-D-galactopyranosyl(=β-lycotetraosyl)-(25 R and S)-spirost-5-en-3β,14α-diol, 3-O-β-lycotetraosyl-22-methoxy-(25 R and S)-furost-5-en-3β,14α,26-triol 26-O-β-D-glucopyranoside, 3-O-β-D-glucopyranosyl-(1->2)-3)>-β-D-glucopyranosyl(1->4)-β-D-galactopyranosyl-22-methoxy-(25 R and S)-furost-5-en-3β,14α,26-triol 26-O-β-D-glucopyranoside and 3-O-β-lycotetraosyl yamogenin, respectively.Moreover, (25 S)-spirost-5-en-3β,14α-diol (7) was isolated from a mixture of the (25 R) and (S) derivatives of PO-a (1) and it was designated as neoprazerigenin A.Keywords - Polygonatum odoratum var. pluriflorum; Liliaceae; neoprazerigenin A; spirostanol glycoside; furostanol glycoside.
- Sugiyama, Mari,Nakano, Kimiko,Tomimatsu, Toshiaki,Nohara, Toshihiro
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p. 1365 - 1372
(2007/10/02)
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- PARTIAL METHYLATION OF METHYL α-D-GLUCOPYRANOSIDE. I. LIQUID CHROMATOGRAPHY OF THE ACETATES OF THE TRI-O-METHYL ETHERS OF METHYL α-D-GLUCOPYRANOSIDE
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A method is described for obtaining the acetates of the tri-O-methyl ethers of methyl α-D-glucopyranoside via the partial methylation of methyl α-D-glucopyranoside and the subsequent preparative liquid chromatography of the acetates of the tri-O-methyl ethers.
- Evtushenko, E. V.,Ovodov, Yu. S.
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- GLYCOSIDES OF MARINE INVERTEBRATES. XV. A NEW TRITERPENE GLYCOSIDE - HOLOTHURIN A1 - FROM CARIBBEAN HOLOTHURIANS OF THE FAMILY HOLOTHURIIDAE
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A glycoside, holothurin A1 has been isolated from the polar glycosidic fractions of the holothurians H. floridana and H. grisea.The complete structure of the glycoside has been established; it is: 3β-3)-O-β-D-glucopyranosyl-(1->4)-O-β-D-quinovopyranosyl-(1->2)-(4-sulfato-β-D-xylopyranosyl)oxy>holosta-9(11)-ene-12α,17α,22ξ-triol.Details of the IR and 1H and 13C NMR spectra of the compounds obtained are given.
- Oleinikova, G. K.,Kuznetsova, T. A.,Ivanova, N. S.,Kalinovskii, A. I.,Rovnykh, N. V.,Elyakov, G. B.
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p. 430 - 434
(2007/10/02)
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- Steroidal glycosides of Tribulus terrestris Linn.
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Besides β-sitosterol-β-D-glucoside and dioscin, two new steroidal glycosides, neohecogenin glucoside and tribulosin, isolated from the aerial part of Tribulus terrestris Linn. were respectively shown to be neohecogenin-3-O-β-D-glucopyranoside (2) and neotigogenin-3-O-β-D-xylopyranosyl(1->2)-3)>-β-D-glucopyranosyl(1->4)-2)>-β-D-galactopyranoside (7).
- Mahato, Shashi B.,Sahu, Niranjan P.,Ganguly, Amar N.,Miyahara, Kazumoto,Kawasaki, Toshio
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p. 2405 - 2410
(2007/10/02)
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