无邻基参与下的β-选择性糖基化反应：3,4-O-双缩醛保护体系的影响
β-Selective Glucosylation in the Absence of Neighboring Group Participation: Influence of the 3,4-O-Bisacetal Protecting System.
作者信息
Crich David, Subramanian Venkataraman, Hutton Thomas K
机构信息
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA.
出版信息
Tetrahedron. 2007 Jun 4;63(23):5042-5049. doi: 10.1016/j.tet.2007.03.128.
Abstract
A 3,4-O-bisacetal 2,6-di-O-benzyl protected thioglucoside is converted to the corresponding glucosyl triflate with 1-benzenesulfinyl piperidine and trifluoromethanesulfonic anhydride. The moderate to excellent β-selectivity exhibited with this glucosyl triflate with a range of alcohols is generally higher than that observed with the more electronically disarmed corresponding 3,4-O-carbonate, for which a possible reason is advanced.
摘要
一种3,4-O-双缩醛2,6-二-O-苄基保护的硫代葡萄糖苷与1-苯亚磺酰基哌啶和三氟甲磺酸酐反应，转化为相应的葡萄糖基三氟甲磺酸酯。这种葡萄糖基三氟甲磺酸酯与一系列醇反应表现出的中等至优异的β选择性通常高于相应的电子效应较弱的3,4-O-碳酸酯所观察到的选择性，并对此提出了一个可能的原因。
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