First synthesis of P-aryl-phosphinosugars, organophosphorus analogues of C-arylglycosides

被引：21

作者：

Cristau, HJ ^{[1
]}

Monbrun, J ^{[1
]}

Schleiss, J ^{[1
]}

Virieux, D ^{[1
]}

Pirat, JL ^{[1
]}

机构：

[1] Ecole Natl Super Chim Montpellier, CNRS, UMR 5076, Chim Organ Lab, F-34296 Montpellier, France

来源：

TETRAHEDRON LETTERS | 2005年 / 46卷 / 21期

关键词：

phostone; sugar analogues; arylphosphinic; polyhydroxylated;

D O I：

10.1016/j.tetlet.2005.03.148

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis and X-ray crystal structure of the first example of arylphosphinosugar are reported. The protected polyhydroxylated 1,2-oxaphosphinane is prepared by a two steps sequence (phenylphosphinate addition on protected mannofuranose followed by intramolecular transesterification) on gram scale. Deprotection of the di-isopropylidene derivative using acidic cation-exchange resin affords the free hydroxy organophosphorus heterocycle analogous to C-arylglycosides. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：3741 / 3744

页数：4

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