A Novel, Industrially‐feasible Synthetic Route to (+)‐Biotin from L‐Cysteine

Author:

Zhang Qiongmei1,Peng Kun1,Bonrath Werner23,Zhang Zili1,Zhu Zhibin1,Xing Yuehan1,Wang Xiaoyan1,Gao Bo1,Medlock Jonathan A.3ORCID

Affiliation:

1. DSM-Firmenich, Process R&D 476 Li Bing Road, Pudong Industrial Area 201203 Shanghai China

2. Werner Bonrath Consulting Luckenbachweg 29 D-79115 Freiburg Germany

3. DSM-Firmenich, Process R&D Wurmisweg 576 4303 Kaiseraugst Switzerland

Abstract

AbstractA novel, industrially viable synthetic route to (+)‐biotin has been developed starting from L‐cysteine via the known key thiolactone intermediate. The route takes advantage of the in‐built stereochemistry of the cysteine starting material and the best features of the two current industrialized processes. The key transformations are the conversion of L‐cysteine into a hydantoin avoiding racemization followed by catalytic cyanation and thiolactonization to form the required thiolactone intermediate. This known intermediate can be readily further transformed into (+)‐biotin.

Publisher

Wiley

Reference29 articles.

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4. M. W. Goldberg L. H. Sternbach ‘Debenzylation of Benzylated Imidazolido-Thiophane Compounds’ US patent 2489238 1949. (Hoffmann-La Roche Inc.).

5. Biotin. II. Synthesis of Biotin

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