α-异麦芽糖苷甲酯的电化学合成。

An electrochemical synthesis of methyl alpha-isomaltoside.

作者信息

Hamann C H, Polligkeit H, Wolf P, Smiatacz Z

机构信息

Fachbereich Chemie, Carl von Ossietzky-Universität, Oldenburg, Germany.

出版信息

Carbohydr Res. 1994 Dec 2;265(1):1-7. doi: 10.1016/0008-6215(94)00218-5.

DOI:10.1016/0008-6215(94)00218-5

PMID:7834646

Abstract

A novel approach has been developed for the synthesis of methyl alpha-isomaltoside (10), comprising, as the first step, electrochemical conversion of the hydroxyl groups of methyl alpha-D-glucopyranoside into the corresponding anions. The anions subsequently react with tetra-O-acetyl-alpha-D-glucopyranosyl bromide to give methyl 2',3',4',6'-tetra-O-acetyl-alpha-isomaltoside (8) as the main product, O-deacetylation of which affords 10. The glycosidation proceeds under complete stereochemical control.

摘要

已开发出一种合成α-异麦芽糖甲酯（10）的新方法，第一步是将α-D-吡喃葡萄糖甲酯的羟基电化学转化为相应的阴离子。这些阴离子随后与四-O-乙酰基-α-D-吡喃葡萄糖基溴反应，得到主要产物2',3',4',6'-四-O-乙酰基-α-异麦芽糖甲酯（8），对其进行O-脱乙酰化得到10。糖苷化反应在完全立体化学控制下进行。