Novel rearrangement reactions in the fluorination of methyl 3-C-methyl-3-nitro-alpha-L-hexopyranosides by the DAST reagent

被引:21
作者
BorracheroMoya, P [1 ]
CabreraEscribano, F [1 ]
GomezGuillen, M [1 ]
MadridDiaz, F [1 ]
机构
[1] UNIV SEVILLA, FAC QUIM, DEPT QUIM ORGAN PROF GARCIA GONZALEZ, E-41071 SEVILLE, SPAIN
关键词
D O I
10.1016/S0040-4039(96)02479-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple method for the preparation of 1-fluoro- and/or 5-fluoro-3-branched-chain sugar derivatives by reaction of DAST with methyl 3-C-methyl-3-nitro-alpha-L-hexopyranosides is described. The reaction involves rearrangement with or without ring contraction, depending on the 1,2 relative configuration and the presence of a free OH group at C-4 in the substrate. A new, useful aldehydo-sugar ramified at 0-3 is easily accessible in good yield by the route reported here. (C) 1997, Elsevier Science Ltd.
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页码:1231 / 1234
页数:4
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