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

HOULTON, JS; MOTHERWELL, WB; ROSS, BC; TOZER, MJ; WILLIAMS, DJ; SLAWIN, AMZ; (1993) A CONVENIENT STRATEGY FOR REPLACEMENT OF THE ANOMERIC HYDROXYL GROUP BY DIFLUOROMETHYL FUNCTIONALITY IN CARBOHYDRATE-DERIVATIVES. TETRAHEDRON , 49 (36) 8087 - 8106.

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Abstract

A series of carbohydrate gem-difluoroenol ethers are readily prepared by the reaction of the corresponding lactones with dibromodifluoromethane, tris(dimethylamino)phosphine and zinc. Subsequent catalytic hydrogenation provides difluoromethyl C-glycoside analogues in which the exocyclic oxygen atom has been replaced by a difluoromethylene unit.

Type:Article
Title:A CONVENIENT STRATEGY FOR REPLACEMENT OF THE ANOMERIC HYDROXYL GROUP BY DIFLUOROMETHYL FUNCTIONALITY IN CARBOHYDRATE-DERIVATIVES
Keywords:NUCLEOSIDES, INHIBITORS, FLUORINE
UCL classification:UCL > School of BEAMS > Faculty of Maths and Physical Sciences > Chemistry

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