1,720,986 research outputs found

    A Green and Regioselective Acetylation of Thioglycoside with Ethyl Acetate

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    Treatment of saccharidic polyols in ethyl acetate with catalytic sulfuric acid leads to the corresponding primary monoacetate derivatives in good yields. The transesterification was realized by simple stirring without rigorous exclusion of moisture or oxygen. Our protocol is applicable to the regioselective mono-acetylation of amino sugars having different substituents at the 2-positions

    Rearrangement reactions in the fluorination of D-glucopyranoside at the C-4 position by DAST

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    Attempts to synthesize 4-deoxy-4-fluoro-KRN-7000 (2), a potential immune adjuvant, by fluorination of 4-hydroxy of alpha-D-glucopyranoside using DAST, were not successful. Instead, the unusual 5-deoxy-5-fluoro beta-L-altrofurnoside and the corresponding 4-deoxy-4-fluoro alpha-D-glucopyranoside with retained configuration were obtained. In the presence of polar solvents, the reaction afforded the epoxide product, suggesting the bicyclic oxiranium ion intermediate to be involved in this reaction. Compound 2 was eventually achieved by treating 4-methanesufonated glucopyranoside with fluoride ion and found to be a weak agonist for CD1d and NKT cell activation. (C) 2016 Elsevier Ltd. All rights reserved

    New Development of Glycan Arrays

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    The development of glycan arrays has enabled the high- sensitivity and high-throughput analysis of carbohydrate- protein interactions and contributed to significant advances in glycomics. A number of new array platforms that allow for qualitative and quantitative analysis of mono-and multivalent interactions on surfaces have been developed recently. Glycan arrays are not only a powerful tool for basic research, but also a promising technique for medical diagnosis, and detection of pathogens and cancers. These studies also have led to the design of efficient carbohydrate-based antimicrobial or anticancer vaccines
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