Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group using HCl/dioxane (4 M)

被引：125

作者：

Han, G ^{[1
]}

Tamaki, M ^{[1
]}

Hruby, V ^{[1
]}

机构：

[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

来源：

JOURNAL OF PEPTIDE RESEARCH | 2001年 / 58卷 / 04期

关键词：

Boc; dioxane; hydrogen chloride; selective deprotection; tert-butyl ester;

D O I：

10.1034/j.1399-3011.2001.00935.x

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

Fast, efficient and selective deprotection of the tert-butoxycarbonyl (Boc) group of various amino acids and peptides was achieved by using: hydrogen chloride (4 m) in anhydrous dioxane solution for 30 min at room temperature. In the cases studied in our laboratory, this protocol provided superior selectivity to deprotect N-alpha-Boc groups in the presence of tert-butyl esters and tert-butyl ethers, including thio-tert-butyl ethers, but not phenolic tert-butyl ethers.

引用

页码：338 / 341

页数：4

共 8 条

[1]

CRAY CJ, 1969, TETRAHEDRON LETT, P2447

[2]

Fuller WD, 1996, BIOPOLYMERS, V40, P183, DOI 10.1002/(SICI)1097-0282(1996)40:2<183::AID-BIP1>3.0.CO

[3]

2-S

[4] SELECTIVE REMOVAL OF AN N-BOC PROTECTING GROUP IN THE PRESENCE OF A TERT-BUTYL ESTER AND OTHER ACID-SENSITIVE GROUPS [J].