Mild, selective cleavage of amino acid and peptide beta-(trimethylsilyl)ethoxymethyl (SEM) esters by magnesium bromide

被引：18

作者：

Chen, WC ^{[1
]}

Vera, MD ^{[1
]}

Joullie, MM ^{[1
]}

机构：

[1] UNIV PENN,DEPT CHEM,PHILADELPHIA,PA 19014

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 23期

基金：

美国国家卫生研究院;

关键词：

D O I：

10.1016/S0040-4039(97)00863-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Magnesium bromide etherate has been previously shown to cleave beta-(trimethylsilyl)ethoxymethyl (SEM) esters of aliphatic acids. This methodology has now been extended to amino acid and peptide derivatives in the presence of protecting groups typically encountered in peptide chemistry, including the Boc, Cbz, Fmoc and Tree carbamates as well as benzyl-, tert-butyl- and tert-butyldimethylsilyl ethers. The stability of fluoride sensitive protecting groups to magnesium bromide allows for added selectivity in the removal of SEM esters in organic synthesis. (C) 1997 Elsevier Science Ltd.

引用

页码：4025 / 4028

页数：4

共 5 条

[1]

GREENE TW, 1991, PROTECTIVE GROUPS OR

[2] MILD DEPROTECTION OF METHOXYMETHYL ESTERS, METHYLTHIOMETHYL ESTERS, METHOXYETHOXYMETHYL ESTERS, AND BETA-(TRIMETHYLSILYL)ETHOXYMETHYL ESTERS WITH MAGNESIUM BROMIDE IN ETHER [J].