PRACTICAL SYNTHESIS OF A C-GLYCOSYL FLAVONOID VIA O-]C GLYCOSIDE REARRANGEMENT

Authors
KUMAZAWA T OHKI K ISHIDA M SATO S ONODERA JI MATSUBA S
Citation
T. Kumazawa et al., PRACTICAL SYNTHESIS OF A C-GLYCOSYL FLAVONOID VIA O-]C GLYCOSIDE REARRANGEMENT, Bulletin of the Chemical Society of Japan, 68(5), 1995, pp. 1379-1384
Citations number
23
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
68
Issue
5
Year of publication
1995
Pages
1379 - 1384
Database
ISI
SICI code
0009-2673(1995)68:5<1379:PSOACF>2.0.ZU;2-6
Abstract
The C-glycosylation of 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl f luoride and 2-acetylphloroglucinol 3,5-bis(alkyl ether) in the presenc e of boron trifluoride etherate as an activator stereoselectively gave the beta-C-glucoside in a good yield via O-->C glycoside rearrangemen t. Subsequently, aldol condensation of the C-glucoside with benzaldehy de afforded the corresponding beta-C glucosyl chalcone in a good yield .