Regio- and chemoselective reductive cleavage of 4,6-O-benzylidene-type acetals of hexopyranosides using BH3•THF-TMSOTf

被引：57

作者：

Daragics, Katalin ^{[1
]}

Fuegedi, Peter ^{[1
]}

机构：

[1] Hungarian Acad Sci, Chem Res Ctr, Dept Carbohydrate Chem, H-1025 Budapest, Hungary

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 24期

关键词：

Carbohydrates; Benzylidene acetals; Reductive ring opening; Regioselective; CARBOHYDRATE BENZYLIDENE ACETALS; ALUMINUM-CHLORIDE; RING-CLEAVAGE; REGIOSELECTIVITY; DERIVATIVES; OPENINGS; BORANE; EFFICIENT; HYDROGENOLYSIS; REAGENT;

D O I：

10.1016/j.tetlet.2009.03.194

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Benzylidene-type cyclic acetals of carbohydrates undergo efficient reductive ring opening using BH3 center dot THF and a catalytic amount of TMSOTf at room temperature. 4,6-O-Benzylidene-hexopyranosides afford the corresponding 4-O-benzyl ethers exclusively, in high yields. Other benzylidene-type acetals, such as naphthylmethylene and 4-methoxybenzylidene acetals are also cleaved with the same reagent. The conversions are highly regio- and stereoselective and afford benzyl-type ethers in excellent yields. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2914 / 2916

页数：3

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