Synthesis and L-fucosidase inhibitory potency of a cyclic sugar imine and its pyrrolidine analogue

被引：20

作者：

Behr, Jean-Bernard ^{[1
]}

Pearson, Morwenna S. M. ^{[1
]}

Bello, Claudia ^{[2
]}

Vogel, Pierre ^{[2
]}

Plantier-Royon, Richard ^{[1
]}

机构：

[1] Inst Chim Mol Reims, CNRS, UFR Sci, UMR 6229, F-51687 Reims 2, France

[2] Ecole Polytech Fed Lausanne, Lab Glycochim & Synth Asymetr, BCH, CH-1015 Lausanne, Switzerland

来源：

TETRAHEDRON-ASYMMETRY | 2008年 / 19卷 / 15期

基金：

瑞士国家科学基金会;

关键词：

D O I：

10.1016/j.tetasy.2008.06.019

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The synthesis of a fully deprotected ketimine-type iminosugar is reported, starting from commercial D-mannose diacetonide. An appropriate solvent system was critical for the success of the key tandem addition/cyclization reaction. Reduction of the imine was also achieved to yield the corresponding pyrrolidine in a stereoselective manner. The cyclic sugar imine displayed modest fucosidase inhibitory activity when compared to the saturated analogue. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：1829 / 1832

页数：4

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