Protecting Group for Carboxyl Function : Mild and Facile Cleavage of 2-Cyanoethyl Ester under Non-hydrolytic Conditions

Yasuyuki KITA; Hiroshi MAEDA; Fumie TAKAHASHI; Seiji FUKUI; Toshihisa OGAWA; Katsuo HATAYAMA

doi:10.1248/cpb.42.147

Yasuyuki KITA, Hiroshi MAEDA, Fumie TAKAHASHI, Seiji FUKUI, Toshihisa OGAWA, Katsuo HATAYAMA

Author information

Keywords: 2-cyanoethyl ester, carboxyl protecting group, tetrabutylammonium fluoride, deprotection, β-elimination, peptide synthesis

JOURNAL FREE ACCESS

1994 Volume 42 Issue 1 Pages 147-150

DOI https://doi.org/10.1248/cpb.42.147

Details

Abstract

The use of the 2-cyanoethyl group for carboxyl-protection is described. This group was readily introduced by esterification using ethylene cyanohydrin and the deprotection was carried out under mild conditions using tetrabutylammonium fluoride in dimethylformamide-tetrahydrofuran.

Corresponding author

Register with J-STAGE for free!