Regio and stereoselective opening of chiral cyclic sulfates with MgBr2Et2O: A practical strategy for the synthesis of (2R,3S)-(-)-N-benzoyl-3-phenylisoserine ethyl ester (taxol side chain)

Authors
Nandanan, E Phukan, P Sudalai, A
Citation
E. Nandanan et al., Regio and stereoselective opening of chiral cyclic sulfates with MgBr2Et2O: A practical strategy for the synthesis of (2R,3S)-(-)-N-benzoyl-3-phenylisoserine ethyl ester (taxol side chain), I J CHEM B, 38(3), 1999, pp. 283-286
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY
ISSN journal
03764699 → ACNP
Volume
38
Issue
3
Year of publication
1999
Pages
283 - 286
Database
ISI
SICI code
0376-4699(199903)38:3<283:RASOOC>2.0.ZU;2-8
Abstract
The reaction of 4(S)-carbethoxy-5(R)-phenyl-1,3,2-dioxathiolane-2,2-dioxide 4 with MgBr2-Et2O readily proceeding. regio- and stereoselectively at the benzylic position to afford the desired bromohydrin 5 in excellent yield wh ich led to an improved process for the synthesis of (2R, 3S)-(-)-N-benzoyl- 3-phenylisoserine ethyl ester 8 (taxol C13 side chain) in excellent yield a nd optical purity.