Efficient Preparation of a Key Intermediate in the Synthesis of Roxifiban by Enzymatic Dynamic Kinetic Resolution on Large Scale
Organic Process Research & Development2003Vol. 8(1), pp. 22–27
Citations Over Time
Jaan A. Pesti, Jinguao Yin, Linhua Zhang, Luigi Anzalone, Robert E. Waltermire, Philip Ma, Edward Gorko, Pat N. Confalone, Joseph Fortunak, Charlotte Silverman, John A. Blackwell, Junyong Chung, Michael D. Hrytsak, Mary Cooke, Lakisha Powell, Charles Ray
Abstract
Additional information is presented for the transformation of a kinetic resolution into a dynamic kinetic resolution of the isobutyl ester 5b to form the acid 2 in high yield and ee via the intermediacy of a thioester 6c, (Pesti, J. A.; Yin, J.; Zhang, L.-H; Anzalone, L. J. Am. Chem. Soc. 2001, 123, 11075−11076.). The development of optimized reaction conditions for the preparation of 6c, its dynamic kinetic resolution to 2, and the scale-up of both reactions into a pilot plant are described.
Related Papers
- → Stability of thioester intermediates in ubiquitin‐like modifications(2009)22 cited
- → Development of a sufficiently reactive thioalkylester involving the side‐chain thiol of cysteine applicable for kinetically controlled ligation(2015)8 cited
- → An Fmoc Compatible, O to S Shift-Mediated Procedure for the Preparation of C-Terminal Thioester Peptides(2013)13 cited
- → Thioester ligation using peptide hydrazides as crypto-thioesters(2023)1 cited
- → ChemInform Abstract: STUDIES ON HETEROCYCLIC CHEMISTRY. PART 24. SYNTHESES OF THE 4‐ARYLISOTHIAZOL‐3‐YL O‐THIOESTERS UTILIZING THE S‐THIOESTER → O‐THIOESTER REARRANGEMENTS OF THE 4‐ARYL‐5‐THIOXO‐3‐ISOTHIAZOLIN‐3‐YL S‐THIOESTERS INDUCED BY ACYLATION REAGENTS, PERACID, OR N‐BROMOSUCCINIMIDE(1981)