A synthetic route from D-glucose to D-myo-inositol-1,4,5-tris(dihydrogenphosphate):: use of an unusual ene reaction and the Bu2SnCl2/Bu2SnH2 reagent

被引：6

作者：

Clive, DLJ ^{[1
]}

He, X ^{[1
]}

Postema, MHD ^{[1
]}

Mashimbye, MJ ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 24期

基金：

加拿大自然科学与工程研究理事会;

关键词：

D O I：

10.1016/S0040-4039(98)00792-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

D-Glucose was converted into the propargylsilane aldehyde 3, which underwent ring closure with retention of silicon, in the presence of camphorsulfonic acid, to give 5, and this was elaborated, via ketone 22, into 2, which had previously been transformed into D-myo-inositol-1,4,5-tris(dihydrogenphosphate). A crucial step in the synthesis is the stereoselective reduction of 22 with Bu2SnCl2/Bu2SnH2, a reagent system that shows a strong preference for generating equatorial alcohols. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4231 / 4234

页数：4

共 30 条

[1]

[Anonymous], 1993, The inositol phosphates: chemical synthesis and biological significance

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