RETENTION AND APPARENT INVERSION DURING AZIDE DISPLACEMENT OF ALPHA-TRIFLATES OF 1,5-LACTONES

被引:42
作者
BRUCE, I [1 ]
FLEET, GWJ [1 ]
GIRDHAR, A [1 ]
HARALDSSON, M [1 ]
PEACH, JM [1 ]
WATKIN, DJ [1 ]
机构
[1] CHEM CRYSTALLOG LAB,OXFORD OX1 3PD,ENGLAND
关键词
D O I
10.1016/S0040-4020(01)97581-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reactions of azide ion with 2-O-trifluoromethanesulphonates of both 34:67-di-O-isopropylidene-D-glycero-D-talo-hepton-0-15-lactone and of 34;67-di-O-isopropylidene-D-glycero-D-galacto-heptono-1-5-lactone give predominantly 2-azido-2-deoxy-3 4:6 7-di-O-isopropylidene-D-glycero-D-galacto 5-lactone initially which then isomerises under the reaction conditions to 2-azido-2-deoxy-34:67-di-O-isopropylidene-Dglycerol-D-talo-heptono-1 X-ray crystal structure analyses of 34;67-di-O-isopropylidene-D-glyceroD-1-talo-heptono-1 5-lactone. and 2-azido-2-deoxy-3 4:6 7-di-O-isopropylidene-D-glycero-D-talo-heptono-15-lactone are reported. © 1990.
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页码:19 / 32
页数:14
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