A facile chemoselective deacetylation in the presence of benzoyl and p-bromobenzoyl groups using p-toluenesulfonic acid

被引：30

作者：

González, AG ^{[1
]}

Brouard, I ^{[1
]}

León, F ^{[1
]}

Padrón, JI ^{[1
]}

Bermejo, J ^{[1
]}

机构：

[1] CSIC, Inst Prod Nat & Agrobiol, Inst Univ Bioorgan Antonio Gonzalez, Tenerife 38206, Canary Islands, Spain

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 18期

关键词：

D O I：

10.1016/S0040-4039(01)00406-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The acetyl group was chemoselectively cleaved in the presence of p-toluenesulfonic acid (p-TsOH) in CH2Cl2/MeOH without affecting the benzoyl (benzoate and p-bromobenzoate) groups and no transesterification product was observed. The treatment of protected carbohydrates with p-TsOH .H2O at room temperature usually required a longer reaction time than at 40 degreesC. Other types of sulfonic acid such as 10-camphorsulfonic (CSA) led to similar res;lts. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：3187 / 3188

页数：2

共 15 条

[1]

BAPTISTELLA LHB, 1989, SYNTHESIS-STUTTGART, P436

[2]

BLAY G, 1989, SYNTHESIS-STUTTGART, P438

[3] SELECTIVE REMOVAL OF O-ACETYL GROUPS IN THE PRESENCE OF O-BENZOYL GROUPS BY ACID-CATALYZED METHANOLYSIS [J].