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

被引:69
作者
HOULTON, JS
MOTHERWELL, WB
ROSS, BC
TOZER, MJ
WILLIAMS, DJ
SLAWIN, AMZ
机构
[1] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND
[2] GLAXO GRP RES LTD,WARE SG12 0DJ,HERTS,ENGLAND
[3] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,CHEM CRYSTALLOG LAB,LONDON SW7 2AY,ENGLAND
关键词
D O I
10.1016/S0040-4020(01)88029-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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Subsequent catalytic hydrogenation provides difluoromethyl C-glycoside analogues in which the exocyclic oxygen atom has been replaced by a difluoromethylene unit.
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页码:8087 / 8106
页数:20
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