SYNTHESIS OF (2R,3S)-3-[(BENZYLOXYCARBONYL)OXY]-2-FLUORO-TETRADECANOIC-ACID

被引：10

作者：

SHIOZAKI, M

KOBAYASHI, Y

ARAI, M

机构：

[1] New Lead Research Laboratories, Sankyo Co., Ltd. Hiromachi 1-2-58, Shinagawa-ku, Tokyo

来源：

TETRAHEDRON | 1991年 / 47卷 / 34期

关键词：

D O I：

10.1016/S0040-4020(01)96156-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active threo-3-[(benzyloxycarbonyl)oxy]-2-fluorotetradecanoic acid, (2R,3S)-11, was synthesized from 3,4,6-tri-O-acetyl-D-glucal via methyl uronate derivative (5). Reaction of 5 with octylidene triphenylphosphorane followed by treatment with DAST yielded methyl 2-fluorotetradecenoate derivative (2R,3S)-7, from which (2R,3S)-11 was achieved in four steps. The enantiomer was obtained by the resolution of racemic 8.

引用

页码：7021 / 7028

页数：8

共 10 条

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