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

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 07期

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.

引用

页码：1231 / 1234

页数：4

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