A novel synthesis of D-galactofuranosyl, D-glucofuranosyl and D-mannofuranosyl 1-phosphates based on remote activation of new and free hexofuranosyl donors

被引:32
作者
Ferrières, V [1 ]
Blanchard, S [1 ]
Fischer, D [1 ]
Plusquellec, D [1 ]
机构
[1] Ecole Natl Super Chim Rennes, CNRS, UMR 6052, Inst Chim Rennes, F-35700 Rennes, France
关键词
D O I
10.1016/S0960-894X(02)00822-3
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The selective synthesis of 1,2-cis-hexofuranosyl 1-phosphates was readily accomplished according to a procedure based on the 'Remote Activation Concept'. This approach required (i) the preparation of suitable 1,2-trans-hexofuranosyl donors, so that new heterocyclic thiofuranosides were designed and synthesized, (ii) the stereocontrolled phosphorylation of the corresponding unprotected donors and (iii) the simple and fast purification of the resulting anomeric phosphates. This approach showed to be equally efficient in the galactose, glucose and mannose series. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3515 / 3518
页数:4
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