SIMPLE SYNTHESES OF L-FUCOPYRANOSE AND FUCOSIDASE INHIBITORS UTILIZING THE HIGHLY STEREOSELECTIVE METHYLATION OF AN ARABINOFURANOSIDE 5-UROSE DERIVATIVE

Authors
TAKAHASHI S KUZUHARA K
Citation
S. Takahashi et K. Kuzuhara, SIMPLE SYNTHESES OF L-FUCOPYRANOSE AND FUCOSIDASE INHIBITORS UTILIZING THE HIGHLY STEREOSELECTIVE METHYLATION OF AN ARABINOFURANOSIDE 5-UROSE DERIVATIVE, Journal of the Chemical Society. Perkin transactions. I, (5), 1997, pp. 607-612
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I → ACNP
ISSN journal
0300922X
Issue
5
Year of publication
1997
Pages
607 - 612
Database
ISI
SICI code
0300-922X(1997):5<607:SSOLAF>2.0.ZU;2-S
Abstract
The simple syntheses of L-fucopyranose 1 and its three analogues 2-4 a re described. A key reaction is a stereocontrolled elongation by one c arbon unit at the side chain of an alpha-D-arabino-pentodialdo-1,4-fur anoside 9 with MeMgI-ZnCl2 or Me(3)Al. Diastereofacial selectivities o f more than 92% were achieved.