The reaction of acetal-type protective groups in combination with TMSOTf and 2,2′-bipyridyl; mild and chemoselective deprotection and direct conversion to other protective groups

被引：23

作者：

Fujioka, Hiromichi ^{[1
]}

Minamitsuji, Yutaka ^{[1
]}

Kubo, Ozora ^{[1
]}

Senami, Kento ^{[1
]}

Maegawa, Tomohiro ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Pharmaceut Sci, Suita, Osaka 5650871, Japan

来源：

TETRAHEDRON | 2011年 / 67卷 / 16期

基金：

日本学术振兴会;

关键词：

Deprotection; Chemoselective; MOM-type ether; 2,2 '-Bipyridyl acetal; WEAKLY ELECTROPHILIC SALTS; ASYMMETRIC TOTAL-SYNTHESIS; METHOXYMETHYL-ETHERS; 2-(TRIMETHYLSILYL)ETHYL GLYCOSIDES; 2-TRIMETHYLSILYLETHYL GLYCOSIDES; SELECTIVE DEPROTECTION; EFFICIENT DEPROTECTION; DIMETHYLBORON BROMIDE; HIGHLY EFFICIENT; FORMAL SYNTHESIS;

D O I：

10.1016/j.tet.2011.02.048

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and chemoselective deprotection method of various acetal-type protective groups, such as MOM, MEM, BOM, and SEM ethers, has been developed. The combination of TMSOTf and 2,2'-bipyridyl was very effective for the deprotection, and the reaction proceeded via the formation of pyridinium intermediates, which were hydrolyzed to the corresponding alcohols in good to high yields. The features of this method are mild (almost neutral) reaction conditions and the tolerability of acid-sensitive functional groups. This method is also applicable for the direct conversion of MOM ether to BOM or SEM ether using the appropriate alcohols instead of H2O. (C) 2011 Elsevier Ltd. All rights reserved.

引用

页码：2949 / 2960

页数：12

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