Diastereoselective synthesis of novel iminosugar-containing UDP-Galf mimics:: Potential inhibitors of UDP-gal mutase and UDP-Galf transferases

被引：48

作者：

Liautard, Virginie

Christina, Alphert E.

Desvergnes, Valerie

Martin, Olivier R.

机构：

[1] CNRS, Inst Chim Organ & Analyt, F-45067 Orleans, France

[2] Univ Orleans, F-45067 Orleans, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 19期

关键词：

D O I：

10.1021/jo061130e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tetra-O-benzyl-D-glucofuranose was converted into uridine diphosphono-beta-Galf mimics based on an iminosugar skeleton linked to UMP by a 2-hydroxypropyl tether. The synthesis is based on the highly regio- and stereoselective cycloaddition of an original uridin-5'-yl allylphosphonate with a 1,4-dideoxy-1,4-iminogalactitol-derived cyclic nitrone, followed by the reductive elaboration of the cycloaddition product. The resulting iminogalactose-UMP conjugates are novel sugar nucleotide mimics which could be useful as inhibitors of UDP-Gal mutase and UDP-Galf transferases.

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收藏

页码：7337 / 7345

页数：9

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