芳基硼酸酯催化的2-脱氧糖衍生物的脱水糖基化反应

Dehydrative glycosidations of 2-deoxysugar derivatives catalyzed by an arylboronic ester.

作者信息

Manhas Sanjay, Taylor Mark S

机构信息

Department of Chemistry, University of Toronto, 80 St. George St., Toronto, ON, M5S 3H6, Canada.

出版信息

Carbohydr Res. 2018 Dec;470:42-49. doi: 10.1016/j.carres.2018.10.002. Epub 2018 Oct 15.

DOI:10.1016/j.carres.2018.10.002

PMID:30368103

Abstract

An N-methylpyridinium-4-boronic ester acts as a catalyst for dehydrative glycosidations of 2-deoxy sugar-derived hemiacetals. The catalytic protocol is tolerant of functionalized acceptors, including alcohols bearing isopropylidene ketal, tert-butyl carbamate or benzyl carbamate groups. The results demonstrate that organoboron-catalyzed substitution reactions of alcohols, which have previously been conducted on π-activated (benzylic, allylic or propargylic) substrates, can also be used to achieve C-O bond formation from carbohydrate-derived hemiacetals.

摘要

N-甲基吡啶-4-硼酸酯可作为2-脱氧糖衍生的半缩醛脱水糖苷化反应的催化剂。该催化方法适用于官能化的受体，包括带有异亚丙基缩酮、叔丁基氨基甲酸酯或苄基氨基甲酸酯基团的醇。结果表明，此前在π-活化（苄基、烯丙基或炔丙基）底物上进行的有机硼催化的醇取代反应，也可用于实现由碳水化合物衍生的半缩醛形成C-O键。