A CONVENIENT STRATEGY FOR REPLACEMENT OF THE ANOMERIC HYDROXYL GROUP BY DIFLUOROMETHYL FUNCTIONALITY IN CARBOHYDRATE-DERIVATIVES

Authors
HOULTON JS MOTHERWELL WB ROSS BC TOZER MJ WILLIAMS DJ SLAWIN AMZ
Citation
Js. Houlton et al., A CONVENIENT STRATEGY FOR REPLACEMENT OF THE ANOMERIC HYDROXYL GROUP BY DIFLUOROMETHYL FUNCTIONALITY IN CARBOHYDRATE-DERIVATIVES, Tetrahedron, 49(36), 1993, pp. 8087-8106
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
36
Year of publication
1993
Pages
8087 - 8106
Database
ISI
SICI code
0040-4020(1993)49:36<8087:ACSFRO>2.0.ZU;2-D
Abstract
A series of carbohydrate gem-difluoroenol ethers are readily prepared by the reaction of the corresponding lactones with dibromodifluorometh ane, tris(dimethylamino)phosphine and zinc. Subsequent catalytic hydro genation provides difluoromethyl C-glycoside analogues in which the ex ocyclic oxygen atom has been replaced by a difluoromethylene unit.