A simple method for the preparation of aryl 1-thioglycosides is described. The reaction of D-glucose pentaacetate or 2-acetamido-2-deoxy-D-glucose tetraacetate with arenethiols in the presence of zinc chloride under fusion conditions formed their 1-thioglycosides in good yields. Some Lewis acids in addition to zinc chloride were studied as catalysts in the reaction.
Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI<sub>3</sub>
作者:Shiue-Shien Weng、Kun-Yi Hsieh、Zih-Jian Zeng
DOI:10.1002/jccs.201600828
日期:2017.5
Thioglycosylation of 1‐hydroxyl glycosides catalyzed by in situ‐generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per‐modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation
α- and β-thioglycosides serve as effective nucleophiles for Buchwald–Hartwig cross-couplingreactions using functionalized (hetero)arylhalides. The functional group tolerance on the electrophilic partner is typically high, both benzyl and acetate protecting groups on the carbohydrate are tolerated, and anomer selectivities of thioglycosides are high in all cases studied. The efficiency of this general
Site‐Selective S‐Arylation of 1‐Thiosugars with Aryl Thianthrenium Salts through Copper(I)‐Mediated, Photoredox‐ Catalyzed Reactions
作者:Yini Fang、Qing Liang、Lingling Shi、Jiayang Wen、Xinzhang Liu、Xuerui Hong、Xiaoming Zha、Fei Ji
DOI:10.1002/adsc.202400121
日期:2024.5.21
for the synthesis of aryl thioglycosides from the aryl thianthrenium salts and 1‐thiosugars is achieved by copper(I)‐mediated, photoredox‐catalyzed reactions. The desired products could be obtained in 32% to 78% yield after irradiation with 34 W blue light at room temperature. Various functional groups, especially including halogen groups, were well tolerated under standard reaction conditions. This strategy
Diastereoselective thioglycosylation of peracetylated glycosides catalyzed by in situ generated iron(III) iodide from elemental iodine and iron
作者:Shiue-Shien Weng
DOI:10.1016/j.tetlet.2009.07.077
日期:2009.11
A facile in situ preparation of Fe(III) iodide from cheap, abundant elemental iodine and iron metal served as an efficient catalyst for the thioglycosylation of peracetylated glycosides with various alkyl and aryl mercaptans. Due to neighboring participation, the anomerically pure beta-thioglycosides were obtained in good to high yields with exclusive diastereocontrol. (C) 2009 Published by Elsevier Ltd.