- Anti-dengue, cytotoxicity, antifungal, and in silico study of the newly synthesized 3-O-Phospo-α-D-glucopyranuronic acid compound
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The aim of the current study was to synthesize new bioactive compounds and evaluate their therapeutic relevance.The chemical structure of compound 7 (methyl 3-O-phospo-D-glucopyranuronic acid was elucidated by physical and advance spectral technique. Also, this compound was assessed for various in vitro biological screening. The results showed that compound 7 has promising antifungal activity against selected fungal strains. Computational study was also carried out to find antimalarial efficacy of the synthesized compounds. Compounds (2-7) were tested for cytotoxicity by MTT assay, and no considerable cytotoxicity was observed.Molecular docking studywas performed to predict the bindingmodes of newcompound (7).Thedocking results revealed that the compound has strong attraction towards the target protein, as characterized by good bonding networks. On the basis of the acquired results, it can be predicted that compound (7) might show good inhibitory activity against dengue envelope protein.
- Abu-Izneid, Tareq,Rauf, Abdur,Bawazeer, Saud,Wadood, Abdul,Patel, Seema
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Read Online
- Carbohydrate-Derived Metal-Chelator-Triggered Lipids for Liposomal Drug Delivery
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Liposomes are versatile three-dimensional, biomaterial-based frameworks that can spatially enclose a variety of organic and inorganic biomaterials for advanced targeted-delivery applications. Implementation of external-stimuli-controlled release of their cargo will significantly augment their wide application for liposomal drug delivery. This paper presents the synthesis of a carbohydrate-derived lipid, capable of changing its conformation depending on the presence of Zn2+: an active state in the presence of Zn2+ ions and back to an inactive state in the absence of Zn2+ or when exposed to Na2EDTA, a metal chelator with high affinity for Zn2+ ions. This is the first report of a lipid triggered by the presence of a metal chelator. Total internal reflection fluorescence microscopy and a single-liposome study showed that it indeed was possible for the lipid to be incorporated into the bilayer of stable liposomes that remained leakage-free for the fluorescent cargo of the liposomes. On addition of EDTA to the liposomes, their fluorescent cargo could be released as a result of the membrane-incorporated lipids undergoing a conformational change.
- Holmstr?m, Thomas,Galsgaard Malle, Mette,Wu, Shunliang,Jensen, Knud J?rgen,Hatzakis, Nikos S.,Pedersen, Christian Marcus
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supporting information
p. 6917 - 6922
(2021/02/26)
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- Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides
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A phenylselenoglycosylation reaction of glycal derivatives mediated by diphenyl diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-Carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent β-selectivity, resulting in 2-phenylseleno-2-deoxy-β-galactosides and 2-phenylseleno-β-mannosides which are good precursors of 2-deoxy-β-galactosides and β-mannosides, respectively.
- Li, Zhongjun,Meng, Shuai,Yao, Wang,Zhong, Wenhe
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- A General Approach to O-Sulfation by a Sulfur(VI) Fluoride Exchange Reaction
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O-sulfation is an important chemical code widely existing in bioactive molecules, but the scalable and facile synthesis of complex bioactive molecules carrying O-sulfates remains challenging. Reported here is a general approach to O-sulfation by the sulfur(VI) fluoride exchange (SuFEx) reaction between aryl fluorosulfates and silylated hydroxy groups. Efficient sulfate diester formation was achieved through systematic optimization of the electronic properties of aryl fluorosulfates. The versatility of this O-sulfation strategy was demonstrated in the scalable syntheses of a variety of complex molecules carrying sulfate diesters at various positions, including monosaccharides, disaccharides, an amino acid, and a steroid. Selective hydrolytic and hydrogenolytic removal of the aryl masking groups from sulfate diesters yielded the corresponding O-sulfate products in excellent yields. This strategy provides a powerful tool for the synthesis of O-sulfate bioactive compounds.
- Ferraro, Samantha L.,Flynn, James P.,Hwang, Seung,Liu, Chao,Niu, Jia,Yang, Cangjie
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supporting information
p. 18435 - 18441
(2020/08/25)
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- To acetyl cedilanid glucose modified compound liposomes and the use thereof (by machine translation)
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The invention discloses a de-acetyl cedilanid glucose modified compound liposome and its application. Mainly from the cedilanid glucose-based reconstruction, to glucose and 2 - amino glucose as raw material for some molecular modification with the end of the digoxin 3 - hydroxyl at the delivery into connected to acetyl cedilanid glucose-based modified product, in active under the guide of the choose to conform with the requirements of the molecule. By synthesis to acetylation cedilanid glucose modified compounds (2 - O - benzyl - β - D - glucopyranoside - acetyl cedilanid and the like), so as to enhance the anti-cancer effect of such compounds, improve the strength of the titer, prolong the half-life, at the same time the modified compound preparation into the liposome, improve the targeting [...], reduce cardiac toxicity. (by machine translation)
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Paragraph 0017; 0021
(2019/05/22)
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- Chemoenzymatic Synthesis of Advanced Intermediates for Formal Total Syntheses of Tetrodotoxin
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Advanced intermediates for the syntheses of tetrodotoxin reported by the groups of Fukuyama, Alonso, and Sato were prepared. Key steps include the toluene dioxygenase mediated dihydroxylation of either iodobenzene or benzyl acetate. The resulting diene diols were transformed into Fukuyama's intermediate in six steps, into Alonso's intermediate in nine steps, and into Sato's intermediate in ten steps.
- Baidilov, Daler,Rycek, Lukas,Trant, John F.,Froese, Jordan,Murphy, Brennan,Hudlicky, Tomas
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supporting information
p. 10994 - 10998
(2018/06/04)
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- Co2(CO)6-propargyl cation mediates glycosylation reaction by using thioglycoside
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We discovered that the cobalt-propargyl cation can mediate the glycosylation reaction by activating the thioglycoside donor. The glyco-oxacarbenium cation was formed by transferring the thio-aglycone to the cobalt-propargyl cation that was generated from the cobalt-propargylated acceptor in situ via the activating with Lewis acid. The reactivity of the donor (Armed or dis-armed) and the amount of the Lewis acid control the releasing rate of the cobalt-propargyl group.
- Xia, Meng-jie,Yao, Wang,Meng, Xiang-bao,Lou, Qing-hua,Li, Zhong-jun
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p. 2389 - 2392
(2017/05/29)
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- Synthesis and binding affinity analysis of α1-2- and α1-6-O/S-linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors
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The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards α1-2- and α1-6-linked dimannosides with S- or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrene-mediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the α1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the α1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the α1-2-analog displayed very similar binding compared to the O-linked structure.
- Norberg, Oscar,Wu, Bin,Thota, Niranjan,Ge, Jian-Tao,Fauquet, Germain,Saur, Ann-Kathrin,Aastrup, Teodor,Dong, Hai,Yan, Mingdi,Ramstr?m, Olof
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- Synthesis of MeON-neoglycosides of digoxigenin with 6-deoxy- and 2,6-dideoxy-D-glucose derivatives and their anticancer activity
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Cardiac glycosides show anticancer activities and their deoxy-sugar chains are vital for their anticancer effects. In order to study the structure-activity relationship (SAR) of cardiac glycosides toward cancers and get more potent anticancer agents, a series of MeON-neoglycosides of digoxigenin was synthesized and evaluated. First, ten 6-deoxy- and 2,6-dideoxy-D-glucopyranosyl donors were synthesized starting from methyl α-D-glucopyranoside and 2-deoxy-D-glucose. Meanwhile, the digoxigenin was obtained by acidic hydrolysis of commercially available digoxin as glycosyl acceptor. Then, a 22-member MeON-neoglycoside library of digoxigenin was successfully synthesized by neoglycosylation method. Finally, the induction of Nur77 expression and its translocation from the nucleus to cytoplasm together with cytotoxicity of these MeON-neoglycosides were evaluated. The SAR analysis revealed that C3 glycosylation is required for their induction of Nur77 expression. Moreover, some MeON-neoglycosides (2b and 8b) could significant induce the expression of Nur77 and its translocation from the nucleus to cytoplasm. However, these compounds showed no inhibitory effects on the proliferation of cancer cells, suggesting that they may not induce apoptosis of NIH-H460 cancer cells and their underlying potential and application toward cancer cells deserves future study.
- Wang, Dong-dong,Li, Xiao-san,Bao, Yu-zhou,Liu, Jie,Zhang, Xiao-kun,Yao, Xin-sheng,Sun, Xue-Long,Tang, Jin-Shan
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p. 3359 - 3364
(2017/07/07)
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- Regioselective alkylation of carbohydrates and diols: A cheaper iron catalyst, new applications and mechanism
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As an extension of our previous research on the regioselective protection of carbohydrates and diols, we developed an iron catalyst, Fe(dibm)3 (dibm = diisobutyrylmethane), which has an unusually broad catalytic scope in the selective monoalkyl
- Ren, Bo,Yan, Ningning,Gan, Lu
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p. 46257 - 46262
(2017/10/11)
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- Organotin-catalyzed regioselective benzylation of carbohydrate trans-diols
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A convenient approach to regioselective benzylation of carbohydrate trans-diols was developed, where 0.1 equiv. of Bu2SnCl2 and 0.1 equiv. of TBABr were used as the catalysts and 2.0 equiv. of BnCl was used as the benzylation reagent. In most cases, similar or better benzylation regioselectivities and isolated yields were obtained by using catalytic amounts of Bu2SnCl2, rather than stoichiometric amounts of organotin reagents required.
- Xu, Hengfu,Zhang, Ying,Dong, Hai,Lu, Yuchao,Pei, Yuxin,Pei, Zhichao
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supporting information
p. 4039 - 4042
(2017/10/06)
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- An Iron(III) Catalyst with Unusually Broad Substrate Scope in Regioselective Alkylation of Diols and Polyols
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In this study, [Fe(dibm)3] (dibm=diisobutyrylmethane) is shown to have unusually broad scope as a catalyst for the selective monoalkylation of a diverse set of 1,2- and 1,3-diol-containing structures. The mechanism is proposed to proceed via a cyclic dioxolane-type intermediate, formed between the iron(III) species and two adjacent hydroxyl groups. This approach represents the first transition-metal catalysts that are able to replace stoichiometric amounts of organotin reagents in regioselective alkylation. The reactions generally lead to very high regioselectivities and high yields, on par with, or better than, previous methods used for regioselective alkylation.
- Ren, Bo,Ramstr?m, Olof,Zhang, Qiang,Ge, Jiantao,Dong, Hai
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p. 2481 - 2486
(2016/02/12)
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- Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine
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We report a synthetic glycosylation reaction between sucrosyl acceptors and glycosyl fluoride donors to yield the derived trisaccharides. This reaction proceeds at room temperature in an aqueous solvent mixture. Calcium salts and a tertiary amine base promote the reaction with high site-selectivity for either the 3′-position or 1′-position of the fructofuranoside unit. Because nonenzymatic aqueous oligosaccharide syntheses are underdeveloped, mechanistic studies were carried out in order to identify the origin of the selectivity, which we hypothesized was related to the structure of the hydroxyl group array in sucrose. The solution conformation of various monodeoxysucrose analogs revealed the co-operative nature of the hydroxyl groups in mediating both this aqueous glycosyl bond-forming reaction and the site-selectivity at the same time.
- Pelletier, Guillaume,Zwicker, Aaron,Allen, C. Liana,Schepartz, Alanna,Miller, Scott J.
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p. 3175 - 3182
(2016/03/19)
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- Efficient one-pot per-: O -acetylation-thioglycosidation of native sugars, 4,6- O -arylidenation and one-pot 4,6- O -benzylidenation-acetylation of S -/ O -glycosides catalyzed by Mg(OTf)2
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A sequential one-pot per-O-acetylation-S-/O-glycosidation of native mono and disaccharides under solvent free conditions using 0.5 mole% of Mg(OTf)2 as a non-hygroscopic, recyclable catalyst is reported. Regioselective 4,6-O-arylidenation of glycosides and thioglycosides with benzaldehyde or p-methoxybenzaldehyde dimethyl acetal is catalyzed by 10 mole% of Mg(OTf)2 to produce the corresponding 4,6-O-arylidenated product in high yields. Mg(OTf)2 can also mediate sequential one-pot benzylidenation-acetylation of mono and disaccharide based glycosides and thioglycosides in high yield.
- Mukherjee, Mana Mohan,Basu, Nabamita,Chaudhury, Aritra,Ghosh, Rina
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p. 109301 - 109314
(2016/11/30)
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- Enhanced basicity of Ag2O by coordination to soft anions
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In Ag2O-mediated benzylation, the addition of a catalytic amount of KI can greatly improve reactivity. This is usually attributed to the formation of a more reactive iodo-substituted electrophile. However, our studies show this to be due to the enhanced basicity of Ag2O through coordination of soft iodide anions to the silver atom, and show KI to be an initiator. A catalytic amount of Ag2O and NaBr can catalyze transesterification reactions, indicating the enhanced basicity of Ag2O by bromide. We believe that this is a general effect for metal oxides and soft anions, applicable to a wider range of organic reaction systems. All your base belongs to us: In Ag2O-mediated benzylation, the addition of a catalytic amount of KI can greatly improve reactivity. Our studies show this to be attributable to the enhanced basicity of Ag2O through coordination of soft iodide anions to the silver atom, and show KI to be an initiator. Thus, NaBr as an initiator combined with Ag2O has been successfully used to catalyze transesterification reactions.
- Ren, Bo,Wang, Meiyan,Liu, Jingyao,Ge, Jiantao,Dong, Hai
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p. 761 - 765
(2015/03/04)
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- Acceptor Reactivity in the Total Synthesis of Alginate Fragments Containing α- L -Guluronic Acid and β- D -Mannuronic Acid
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The total synthesis of mixed-sequence alginate oligosaccharides, featuring both β-D-mannuronic acid (M) and α-L-guluronic acid (G), is reported for the first time. A set of GM, GMG, GMGM, GMGMG, GMGMGM, GMGMGMG, and GMGGMG alginates was assembled using GM
- Zhang, Qingju,Van Rijssel, Erwin R.,Walvoort, Marthe T. C.,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Codée, Jeroen D. C.
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supporting information
p. 7670 - 7673
(2015/06/25)
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- Exploring glycosylation reactions under continuous-flow conditions
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The industrial development of carbohydrate-based drugs is greatly thwarted by the typical challenges inherent in oligosaccharide synthesis. The practical advantages of continuous-flow synthesis in microreactors (high reproducibility, easy scalability, and fast reaction optimization) may offer an effective support to make carbohydrates more attractive targets for drug-discovery processes. Here we report a systematic exploration of the glycosylation reaction carried out under microfluidic conditions. Trichloroacetimidates and thioglycosides have been investigated as glycosyl donors, using both primary and secondary acceptors. Each microfluidic glycosylation has been compared with the corresponding batch reaction, in order to highlight advantages and drawbacks of microreactors technology. As a significant example of multistep continuous-flow synthesis, we also describe the preparation of a trisaccharide by means of two consecutive glycosylations performed in interconnected microreactors.
- Cancogni, Damiano,Lay, Luigi
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p. 2873 - 2878
(2015/01/16)
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- Modified bleomycin disaccharides exhibiting improved tumor cell targeting
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The bleomycins (BLMs) are a family of antitumor antibiotics used clinically for anticancer chemotherapy. Their antitumor selectivity derives at least in part from their ability to target tumor cells, a property that resides in the carbohydrate moiety of the antitumor agent. In earlier studies, we have demonstrated that the tumor cell selectivity resides in the mannose carbamoyl moiety of the BLM saccharide and that both the BLM disaccharide and monosaccharide containing the carbamoyl moiety were capable of the delivery/uptake of a conjugated cyanine dye into cultured cancer cell lines. Presently, the nature of the participation of the carbamoyl moiety has been explored further to provide compounds of utility for defining the nature of the mechanism of tumor cell recognition and uptake by BLM saccharides and in the hope that more efficient compounds could be identified. A library of seven disaccharide-Cy5 dye conjugates was prepared that are structural analogues of the BLM disaccharide. These differed from the natural BLM disaccharide in the position, orientation, and substitution of the carbamoyl group. Studies of these compounds in four matched sets of tumor and normal cell lines revealed a few that were both tumor cell selective and internalized 2-4-fold more efficiently than the natural BLM disaccharide.
- Madathil, Manikandadas M.,Bhattacharya, Chandrabali,Yu, Zhiqiang,Paul, Rakesh,Rishel, Michael J.,Hecht, Sidney M.
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p. 6800 - 6810
(2015/02/19)
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- SUGAR-LINKER-DRUG CONJUGATES
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The present disclosure relates to sugar-linker-drug conjugates, of the formula [A-B-]n-L-D, wherein A is a saccharide; B is a spacer, n is an integer selected from 1 to 3; L is a linker group and D is a drug having a chemically reactive functional group selected from the group consisting of a primary or secondary amine, hydroxyl, sulfhydryl, carboxyl, aldehyde and ketone. Pharmaceutical compositions comprising the conjugates and methods of using thern are also provided.
- -
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Paragraph 0211
(2014/09/29)
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- SACCHARIDE CONJUGATES
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This invention relates to compounds comprising a saccharide conjugated to an imaging agent or a reporter group, compositions comprising them and methods of using them. Specifically BLM-disaccharide and BLM-monosaccharide conjugates containing different linker groups and an imaging agent or a reporter group are provided for the targeting and imaging of tumors.
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Paragraph 0203; 0204
(2014/10/04)
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- Hydrophobic and hydrophilic balance and its effect on mesophase behaviour in hydroxyalkyl ethers of methyl glucopyranoside
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Four series of monosubstituted methyl a-d-glucopyranoside hydroxyal- kyl ethers were prepared and their thermotropic and lyotropic self-organising properties were investigated in terms of the hydrophobic-hydrophilic balance with respect to their molecular
- Singh, Madan K.,Xu, Rui,Moebs, Sylvie,Kumar, Anil,Queneau, Yves,Cowling, Stephen J.,Goodby, John W.
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p. 5041 - 5049
(2013/06/27)
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- Mannose-binding geometry of pradimicin A
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Pradimicins (PRMs) and benanomicins are the only family of non-peptidic natural products with lectin-like properties, that is, they recognize D-mannopyranoside (Man) in the presence of Ca2+ ions. Coupled with their unique Man binding ability, t
- Nakagawa, Yu,Doi, Takashi,Taketani, Takara,Takegoshi,Igarashi, Yasuhiro,Ito, Yukishige
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p. 10516 - 10525
(2013/08/23)
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- Fluorine-directed β-galactosylation: Chemical glycosylation development by molecular editing
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Validation of the 2-fluoro substituent as an inert steering group to control chemical glycosylation is presented. A molecular editing study has revealed that the exceptional levels of diastereocontrol in glycosylation processes by using 2-fluoro-3,4,6-tri-O-benzyl glucopyranosyl trichloroacetimidate (TCA) scaffolds are a consequence of the 2R,3S,4S stereotriad. This study has also revealed that epimerization at C4, results in a substantial enhancement in β-selectivity (up to β/α 300:1). Copyright
- Durantie, Estelle,Bucher, Christoph,Gilmour, Ryan
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supporting information; experimental part
p. 8208 - 8215
(2012/08/27)
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- α-Selective organocatalytic synthesis of 2-deoxygalactosides
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Alpha rules: A thiourea acts as an efficient organocatalyst for the glycosylation of protected galactals to form oligosaccharides containing a 2-deoxymonosaccharide moiety (see scheme). The reaction is highly stereoselective for α-linkages and proceeds by way of a syn-addition mechanism. Copyright
- Balmond, Edward I.,Coe, Diane M.,Galan, M. Carmen,McGarrigle, Eoghan M.
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p. 9152 - 9155
(2012/10/29)
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- Acceptor-influenced and donor-tuned base-promoted glycosylation
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Base-promoted glycosylation is a recently established stereoselective and regioselective approach for the assembly of di- and oligosaccharides by using partially protected acceptors and glycosyl halide donors. Initial studies were performed on partially methylated acceptor and donor moieties as a model system in order to analyze the key principles of oxyanion reactivities. In this work, extended studies on base-promoted glycosylation are presented by using benzyl protective groups in view of preparative applications. Emphases are placed on the influence of the acceptor anomeric configuration and donor reactivities.
- Boettcher, Stephan,Matwiejuk, Martin,Thiem, Joachim
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p. 413 - 420
(2012/05/05)
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- Disaccharide-containing macrocycles by click chemistry and intramolecular glycosylation
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In this study o- and m-xylylene moieties in combination with a triazolylmethyl moiety have been successfully employed as a relatively rigid spacer system in intramolecular glycosylation reactions. Phenyl 3,4,6-tri-O-benzyl-2-O-propargyl-1-thio-D-glucopyra
- Tiwari, Vinod K.,Kumar, Amit,Schmidt, Richard R.
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supporting information; experimental part
p. 2945 - 2956
(2012/07/27)
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- Ruthenium-catalysed epimerisation of carbohydrate alcohols as a method to determine the equilibria for epimer interconversion in hexopyranosides
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Ruthenium-catalysed epimerisation of secondary carbohydrate alcohols was used to determine the thermodynamic equilibrium between non-anomeric epimers of partially protected glucose, mannose and allose derivatives. A cyclopentadienylruthenium catalyst was used to epimerise each of two pure epimeric alcohols in two separate experiments. The epimerisation reactions were run until the same ratio of epimers was obtained from the two experiments. Secondary carbohydrate alcohols can be epimerised using a cyclopentadienyl ruthenium complex. In this way, the relative stabilities of different hexopyranoside configurations can be determined.
- Ramstadius, Clinton,Traeff, Annika M.,Krumlinde, Patrik,Baeckvall, Jan-E.,Cumpstey, Ian
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experimental part
p. 4455 - 4459
(2011/10/04)
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- Defining oxyanion reactivities in base-promoted glycosylations
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Saccharide oxyanions obtained by base treatment could be employed in glycosylation to give oligosaccharides with high stereo- and regioselectivities.
- Matwiejuk, Martin,Thiem, Joachim
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p. 8379 - 8381
(2011/09/14)
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- New mannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. Part 3: Chiral ketones from sugars
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New d-arabino-hexopyranosid-3-uloses were synthesized by a simple method from mannopyranoside derivatives. The common skeleton possesses a tunable alkoxy group as steric sensor on carbon 2 of the sugar. The new ketones were employed in the dioxirane-mediated epoxidation of a range of trans- and trisubstituted arylalkenes giving enantiomeric excesses from low to good (30-90%). The effect of the size of the steric sensor on the enantioselectivity was also studied. The least bulky group (methoxy group) enhanced the stereoselectivity (up to 90% ee toward triphenylethylene).
- Vega-Pérez, José M.,Peri?án, Ignacio,Vega-Holm, Margarita,Palo-Nieto, Carlos,Iglesias-Guerra, Fernando
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experimental part
p. 7057 - 7065
(2011/10/05)
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- Rapid assembly of gp120 oligosaccharide moieties via one-pot glycosidation-deprotection sequences
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Mannosyl trihaloacetimidate donors equipped with a 2-O-Fmoc group can be effectively activated by catalytic Bi(OTf)3 in glycosidations. Despite the expected participating effect of the Fmoc group, the reaction solvent was found to be decisive f
- Pastore, Antonello,Adinolfi, Matteo,Iadonisi, Alfonso,Valerio, Silvia
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experimental part
p. 1316 - 1323
(2010/10/02)
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- Glycosylation catalyzed by a chiral bronsted acid
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"Chemical equation presented" The use of a chiral Bronsted acid catalyst for the activation of trichloroacetimidate glycosyl donors has been demonstrated for the first time. In toluene the chirality of the acid catalyst is seen to influence the stereochem
- Cox, Daniel J.,Smith, Martin D.,Fairbanks, Antony J.
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supporting information; experimental part
p. 1452 - 1455
(2010/06/20)
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- METHOD FOR PREPARING HEXOSE DERIVATIVES
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A method for preparing hexose derivatives comprises the steps of providing a silylated hexose, treating the silylated hexose with a first carbonyl compound in the presence of a catalyst to form an ketalized hexose, treating the ketalized hexose with a second carbonyl compound followed by treating with a first reductant to form an etherized hexose, and converting the etherized hexose into a target hexose derivative, which can be 2-alcohol hexose, 3-alcohol hexose, 4-alcohol hexose, or a 6-alcohol hexose. In particular, the present invention can prepare the hexose derivatives with highly regioselective scheme to protect individual hydroxyls of monosaccharide units and install an orthogonal protecting group pattern in a one-pot manner
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Page/Page column 2; 5; 7; Sheet 6/9
(2009/05/29)
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- Unusual synthesis of carbohydrate sec-sec ether-linked pseudodisaccharides
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In this paper, we describe the synthesis of sec-sec ether-linked pseudodisaccharides by the coupling of various secondary carbohydrate alcohols with di-O-isopropylidene allose 3-O-triflate. Reactions proceeded with inversion of configuration to give the 3-substituted di-O-isopropylidene glucose derivatives. The crystal structure of a sec-sec ether-linked pseudodisaccharide is reported.
- Akhtar, Tashfeen,Eriksson, Lars,Cumpstey, Ian
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p. 2094 - 2100
(2008/09/21)
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- Direct and convenient method of regioselective benzylation of methyl α-D-glucopyranoside
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A facile and convenient method for the direct preparation of methyl 2,3,6-tri-O-benzyl-α-D-glucopyranoside (2) by the regioselective benzylation of methyl α-D-glucopyranoside (1) with benzyl bromide in the presence of mild bases K2CO3 and KOH (1:1) withou
- Li, Xiaoliu,Li, Zhiwei,Zhang, Pingzhu,Chen, Hua,Ikegami, Shiro
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p. 2195 - 2202
(2008/02/05)
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- Synthesis of some glycosylated derivatives of 2-deoxy-2-fluoro-β- laminaribiosyl fluoride: Another success for glycosynthases
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The synthesis of 4,6-di-O-acetyl-2-deoxy-2-fluoro-3-O-(tetra-O-acetyl-?-d- glucopyranosyl)-?-d-glucosyl fluoride is described. Upon deacetylation and treatment with ?-d-glucopyranosyl fluoride in the presence of a glycosynthase, three products, all 2-deox
- Scaffidi, Adrian,Stick, Robert V.,Stubbs, Keith A.
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- Fluorous dimethylthiocarbamate (FDMTC) protecting groups for alcohols
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N,N-Bis(perfluoroalkyl)thiocarbamoyl chlorides (FDMTC-Cls) were synthesized as reagent for the protection of alcohols. Using the crystalline FDMTC-Cls, the FDMTC groups were introduced into the alcohol molecules in excellent yields in the presence of sodium hydride in THF at room temperature. The products were separated from the excess alcohols by solid-phase extraction with a fluorous reverse-phase silica gel column (Fluorous Solid Phase Extraction; FSPE). The FDMTC groups were readily removed by oxidation with m-chloroperbenzoic acid (m-CPBA) and subsequent hydrolysis with KHCO3.
- Kojima, Masaru,Nakamura, Yutaka,Ishikawa, Takuma,Takeuchi, Seiji
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p. 6309 - 6314
(2007/10/03)
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- DDQ-mediated regioselective de-O-benzylation of pyranosides stilted by a 4,6-O-(2-phenylsulfonyl)ethylidene (PSE) clip
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A model study on diverse 4,6-acetalated O-benzylated D-glucopyranosides was performed to evaluate DDQ-mediated regioselective de-O-benzylation in connection with structural rigidity.
- Cabianca,Tatibouet,Rollin
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p. 317 - 322
(2007/10/03)
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- Nickel(II) chloride-mediated regioselective benzylation and benzoylation of diequatorial vicinal diols
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Ni(II)-chelates of monosaccharide vicinal diols were found to be useful intermediates in regioselective monobenzylation and monobenzoylation. It was observed that the substitution occurs exclusively at the position adjacent to the axially oriented substit
- Gangadharmath, Umesh B.,Demchenko, Alexei V.
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p. 2191 - 2193
(2007/10/03)
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- A New reaction for the direct conversion of 4-azido-4-deoxy-D-galactoside into a 4-deoxy-D-erythro-hexos-3-ulose
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A new one-step reaction has been developed for converting 4-azido-4-deoxy-D-galactoside into 4-deoxy-D-erythro-hexos-3-ulose by phosphoramidites and tetrazole. It is proposed that the new reaction proceeds via an intramolecular Staudinger reaction of the
- Xue, Jie,Wu, Jian,Guo, Zhongwu
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p. 1365 - 1368
(2007/10/03)
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- Synthetic polysaccharides, preparation method therefor and pharmaceutical compositions containing same
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A synthetic polysaccharide including an antithrombin III binding domain consisting of a concatenation of five monosaccharides supporting a total of two carboxylic acid functions and at least four sulpho groups, said domain being directly bound at the non-
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- SmI2/water/amine mediates cleavage of allyl ether protected alcohols: application in carbohydrate synthesis and mechanistic considerations.
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[reaction: see text]. SmI2/H2O/amine provides selective cleavage of unsubstituted allyl ethers in good to excellent yields. This method is therefore useful in deprotection of alcohols and carbohydrates.
- Dahlen, Anders,Sundgren, Andreas,Lahmann, Martina,Oscarson, Stefan,Hilmersson, Goeran
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p. 4085 - 4088
(2007/10/03)
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- Total synthesis of the Glc3Man N-glycan tetrasaccharide
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The total synthesis of the tetrasaccharide Glcα(1→2)Glcα(1→3)Glcα(1→3)ManαOMe, which corresponds to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved by the use of differentially protected selenoglycosides and thioglycosides as glycosyl donors, all of which possessed non-participating protection of the 2-hydroxyl group. Favourable anomeric stereoselectivity was achieved for the glycosylation reactions by the use of ether as solvent, or co-solvent. Global deprotection by catalytic hydrogenation with palladium acetate in a mixture of ethanol and acetic acid yielded the target tetrasaccharide.
- Ennis,Cumpstey,Fairbanks,Butters,Mackeen,Wormald
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p. 9403 - 9411
(2007/10/03)
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- Rearrangements in the course of fluorination by diethylaminosulfur trifluoride at C-2 of glycopyranosides: Some new parameters
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Reaction of a series of 21 glycosides unprotected at O-2 and featuring various configurations with DAST (diethylaminosulfur trifluoride) was monitored by 19F NMR spectroscopy. By means of the diacritical set of data (shift values and coupling c
- Dax, Karl,Albert, Martin,Hammond, David,Illaszewicz, Carina,Purkarthofer, Thomas,Tscherner, Martin,Weber, Hansjoerg
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p. 427 - 448
(2007/10/03)
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- Synthesis of chiral azacrown ethers derived from α-D-glucose and their catalytic properties on the asymmetric Michael addition
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Three types of chiral azacrown ethers have been synthesized from (+)(4,6-O-benzylidene)-O-methyl-α-D-glucopyranoside and their catalytic properties for the asymmetric Michael addition have been investigated; enantioselectivity switching which is dependent on the azacrown ether catalysts has been achieved.
- Itoh, Toshiyuki,Shirakami, Shohei
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- Combinatorial library of moenomycin analogs and methods of producing same
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A combinatorial chemical library of compounds structurally related to the moenomycin class of antibiotics has the formula wherein D is a donor mono- or disaccharide, A is an acceptor monosaccharide, and P-R is a lipophosphoglycerate mimetic group. Members
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- The First Total Syntheses of Enantiomerically Pure Naturally Occuring Ellagitannins Gemin D and its Regioisomer Hippomanin A
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The total syntheses of naturally occuring ellagitannins gemin D (1) and its regioisomer hippomanin A (2) are reported. In addition, the phase-transfer catalyzed benzylation reaction of the 2,3-glucopyranoside diols 3-7 is described. Our studies have illustrated the influence of the structure of 2,3-glucopyranoside diols on the regioselectivity of the phase-transfer catalyzed benzylation at their free 2,3-OH groups. We could show, that both phase-transfer catalyzed benzylations of 2,3-glucopyranoside diols using tetrabutylammonium hydrogensulfate (Bu4NHSO4) or using tetrabutylammonium iodide (Bu4NI) disfavour the formation of the corresponding 3-O-monobenzylated products and preferentially give the 2-O-monobenzylated products. However, the ratio of the generated 2- versus 3-O-mono- and 2,3-dibenzylated products from these reactions also strongly depends upon the nature of the starting materials. The glucopyranosides 3 and 4 are the first examples, which allow the completely regioselective monobenzylation at the 2-OH positions by a phase-transfer catalyzed reaction.
- Khanbabaee, Karamali,Loetzerich, Kerstin,Borges, Markus,Grosser, Mathias
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p. 159 - 166
(2007/10/03)
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- Synthesis of differentially protected phenyl D-thioglucopyranosides and 1-phenyl D-thioglucopyranosiduronic acids
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Convergent syntheses of differentially protected phenyl D- thioglucopyranosides and 1-phenyl D-thioglucopyranosiduronic acids were achieved by employing the Hanessian reaction method.
- Liu, Dashan,Chen, Ru,Hong, Liwu,Sofia, Michael J.
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p. 4951 - 4954
(2007/10/03)
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- Synthesis of 1-O-[(3S,4R)-3-hydroxytetrahydrofuran-4-yl]-α-D- glucopyranoside 3,4,3'-triphosphate as a novel potent IP3 receptor ligand
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1-O-[(3S,4R)-3-Hydroxytetrahydrofuran-4-yl]-α-D-glucopyranoside 3,4,3'- triphosphate (5) was designed and synthesized as a novel IP3 receptor ligand. This compound bound strongly to IP3 receptor from porcine cerebella with an affinity comparable to that of IP3.
- Tatani, Kazuya,Shuto, Satoshi,Ueno, Yoshihito,Matsuda, Akira
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p. 5065 - 5068
(2007/10/03)
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- Synthesis of adenophostin analogues lacking the adenine moiety as novel potent IP3 receptor ligands: Some structural requirements for the significant activity of adenophostin a
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1-O-Tetrahydrofuranyl-α-D-glucopyranose derivatives 5-8 were designed and synthesized as novel IP3 receptor ligands. The glycosidation reactions between fluoroglycosyl donor 23 and tetrahydrofuran derivatives 11-14 as glycosyl acceptors selectively gave the corresponding α-glycosides, which were converted into the target compounds 5-8 via the introduction of phosphate groups using the phosphoramidite method. Among these compounds, 1- O-tetrahydrofuranyl-α-D-glucopyranose trisphosphate derivatives 5 and 8 significantly inhibited the binding of [3H] IP3 to IP3 receptor from porcine cerebella, with IC50 values of 25 and 27 nM, respectively, which were comparable to the affinity of IP3 itself.
- Shuto, Satoshi,Tatani, Kazuya,Ueno, Yoshihito,Matsuda, Akira
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p. 8815 - 8824
(2007/10/03)
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- A synthetic approach to the glycan chain of high mannose type N-glycoprotein
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The syntheses of α-D-glucopyranose-(1→3)-D-mannopyranose, methyl α-D-glucopyranose-(1→3)-α-D-mannopyranoside and methyl α-D-glucopyranose-(1→3)-α-D-mannopyranose-(1→2)-α-D- mannopyranoside are reported. High stereoselectivity was observed during the coupl
- Cherif, Slim,Clavel, Jean-Marc,Monneret, Claude
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p. 1203 - 1218
(2007/10/03)
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