一种温和的乙酰解方法，用于在二 -O-异亚丙基保护的吡喃糖苷体系中区域选择性地去除异亚丙基。
A mild acetolysis procedure for the regioselective removal of isopropylidene in di-O-isopropylidene-protected pyranoside systems.
作者信息
Zhang Pengfei, Ling Chang-Chun
机构信息
Alberta Glycomics Centre, Department of Chemistry, University of Calgary, Calgary, Alberta, T2N 1N4, Canada.
Alberta Glycomics Centre, Department of Chemistry, University of Calgary, Calgary, Alberta, T2N 1N4, Canada.
出版信息
Carbohydr Res. 2017 Jun 5;445:7-13. doi: 10.1016/j.carres.2017.03.021. Epub 2017 Mar 30.
A mild acetolysis method for the regioselective removal of isopropylidene group from di-O-isopropylidene-protected hexopyranosides is reported. O-Isopropylidene-protected intermediates play an important role in carbohydrate chemistry, as they are often found in commercially available furanosyl and pyranosyl materials, and some of them contain more than one O-isopropylidene groups. Methods that permit regioselective removal of O-isopropylidene groups are extremely valuable, as the number of steps in the total synthesis of complex oligosaccharides could be significantly decreased. Here we report that trifluoroacetic acid (TFA)/acetic anhydride (AcO) can be used to regioselectively convert one of the two O-isopropylidene groups to vicinal di-O-acetates in the di-O-isopropylidene-protected galacto- and fructo-pyranosyl systems, and the reagent is compatible with some common functionalities such as sulfonate esters, bromide, azide etc.
报道了一种温和的乙酰解方法，用于从二 -O- 异亚丙基保护的己吡喃糖苷中区域选择性地去除异亚丙基。O- 异亚丙基保护的中间体在碳水化合物化学中起着重要作用，因为它们经常存在于市售的呋喃糖基和吡喃糖基材料中，并且其中一些含有不止一个 O- 异亚丙基。允许区域选择性去除 O- 异亚丙基的方法非常有价值，因为复杂寡糖全合成中的步骤数可以显著减少。在此我们报道，三氟乙酸（TFA）/ 乙酸酐（AcO）可用于在二 -O- 异亚丙基保护的半乳糖和果糖吡喃糖基体系中，将两个 O- 异亚丙基中的一个区域选择性地转化为邻位二 -O- 乙酸酯，并且该试剂与一些常见官能团如磺酸酯、溴化物、叠氮化物等兼容。
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