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

Journal ArticleOPEN 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

Chemical and Pharmaceutical Bulletin (1980) 28(2) 673-676

DOI: 10.1248/cpb.28.673

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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. © 1980, The Pharmaceutical Society of Japan. All rights reserved.

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Kiso, Y., Ukawa, K., Nakamura, S., Ito, K., & Akita, T. (1980). 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. Chemical and Pharmaceutical Bulletin, 28(2), 673–676. https://doi.org/10.1248/cpb.28.673

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

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