HClO4-SiO2 催化下将缩酮温和、高效且选择性地转化为乙酸酯的方法。

A mild, efficient, and selective procedure for transprotection of acetonides to acetates catalyzed with HClO4-SiO2.

机构信息

Department of Applied Chemistry and Pharmacy, Beijing Institute of Technology, Beijing 100081, China.

出版信息

Carbohydr Res. 2009 Nov 23;344(17):2342-8. doi: 10.1016/j.carres.2009.08.035. Epub 2009 Sep 2.

DOI:10.1016/j.carres.2009.08.035

PMID:19783241

Abstract

The transformation of acetonides into acetates is frequently required in synthetic chemistry. An efficient procedure for direct conversion of acetonides into acetates in the presence of HClO(4)-SiO(2) under mild conditions was developed. The acetonides of primary hydroxy groups are directly converted to diacetates, and the anomeric acetonides of furanosides are stereoselectively transformed into the corresponding acetyl beta-d-furanosides with a 2-acetoxyisopropyl group.

摘要

在合成化学中，将缩酮转化为乙酸酯是经常需要的。在温和条件下，使用 HClO(4)-SiO(2)，开发出了将缩酮直接转化为乙酸酯的有效方法。伯羟基缩酮可直接转化为二乙酸酯，呋喃糖苷的端基缩酮可立体选择性地转化为相应的 2-乙酰氧基异丙基-β-D-呋喃糖苷。