1980•Chemical and Pharmaceutical BulletinOpen access

Efficient removal of protecting groups by a 'push-pull' mechanism. II. Deprotection of O-benzyltyrosine with a thioanisole-trifluoroacetic acid system without O-to-C rearrangements.

Yoshiaki Kiso, Kazuko Ukawa, Shizuo Nakamura, Kaoru Ito, Tadashi Akita

Abstract

A thioanisole-trifluoroacetic acid (TFA) system was found to deprotect Tyr (Bzl) quantitatively at 25°within 3 hr by a push-pull mechanism without O-to-C rearrangements. This new deblocking system did not completely deprotect Ser (Bzl) and Thr (Bzl), but deprotected Lys (Z) quantitatively.

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Key concepts: Thioanisole, Trifluoroacetic acid, Chemistry, Mechanism (biology), Protecting group, Stereochemistry, Organic chemistry, Combinatorial chemistry