Synthesis and configuration of the cyclin-dependent kinase inhibitor roscovitine and its enantiomer

The cyclin-dependent kinase inhibitor ( R)-2-(6-benzylamino-9-isopropyl-9 H-purin-2-ylamino)butan-1-ol (roscovitine, 1a), as well as its ( S)-enantiomer 1b, were synthesised. The chemical structure and absolute configuration of both enantiomers was confirmed by X-ray crystallography. Furthermore, hi...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron: asymmetry 2001-11, Vol.12 (20), p.2891-2894
Main Authors: Wang, Shudong, McClue, Steven J., Ferguson, John R., Hull, Jonathan D., Stokes, Steven, Parsons, Simon, Westwood, Robert, Fischer, Peter M.
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The cyclin-dependent kinase inhibitor ( R)-2-(6-benzylamino-9-isopropyl-9 H-purin-2-ylamino)butan-1-ol (roscovitine, 1a), as well as its ( S)-enantiomer 1b, were synthesised. The chemical structure and absolute configuration of both enantiomers was confirmed by X-ray crystallography. Furthermore, high enantiomeric excess (>98%) was demonstrated by chiral chromatography of 1a and 1b, as well as NMR analysis of the diastereomeric Mosher's ester derivatives 2a and 2b. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(01)00471-2