Picolinyl group as an efficient alcohol protecting group:: cleavage with Zn(OAC)2•2H2O under a neutral condition

被引：24

作者：

Baek, JY

Shin, YJ

Jeon, HB

Kim, KS

机构：

[1] Yonsei Univ, Ctr Bioact Mol Hybrids, Seoul 120749, South Korea

[2] Yonsei Univ, Dept Chem, Seoul 120749, South Korea

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 31期

关键词：

picolinate; alcohol protecting group; zinc acetate; copper acetate;

D O I：

10.1016/j.tetlet.2005.05.125

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

As an efficient alcohol protecting group, picolinates (Pic), prepared from the corresponding alcohols using commercial picolinoyl chloride, are readily cleaved by Zn(OAc)(2) or Cu(OAc)(2), even in the presence of other common alcohol protecting groups. Moreover, the picolinyl group at C-2 position in carbohydrates can be selectively cleaved to give methyl 4,6-O-benzylidene-3-O-picolinyl-alpha-D-glucopyranoside and 3-O-picolinyl methyl-4,6-O-benzylidene-alpha-D-galactopyranoside in good yields. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：5143 / 5147

页数：5

共 29 条

[1] Protection of hydroxy groups with diphenylmethyl and 9-fluorenyl trichloroacetimidates - Effect on anomeric stereocontrol [J].