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One-pot carbanionic synthesis of [P.sup.1],[P.sup.2]-diglycosyl, [P.sup.1],[P.sup.1],[P.sup.2]-triglycosyl, and [P.sup.1],[P.sup.1],[P.sup.2],[P.sup.2]-tetraribosyl methylenediphosphonates

Authors :
Grison, Claude
Chibli, Hicham
Barthes, Nicolas
Coutrot, Philippe
Source :
Journal of Organic Chemistry. Oct 13, 2006, Vol. 71 Issue 21, 7978-7988
Publication Year :
2006

Abstract

Novel lithiated carbanions derived from ethyl glycosyl- and diglycosyl methylphosphonates are used in a direct synthesis of [P.sup.1],[P.sup.2]-diglycosyl, [P.sup.1],[P.sup.1],[P.sup.2]-triglycosyl, and [P.sup.1],[P.sup.1],[P.sup.2],[P.sup.2]-tetraribosyl methylenediphosphonates involving a one-pot methylidenediphosphonylation of sugars. This new and direct access to di-, tri- or tetraglycosyl methylenediphosphonates can be used in the preparation of compounds of biological interest, if chemoselective hydrolysis of the ethyl ester in the final products is improved.

Details

Language :
English
ISSN :
00223263
Volume :
71
Issue :
21
Database :
Gale General OneFile
Journal :
Journal of Organic Chemistry
Publication Type :
Academic Journal
Accession number :
edsgcl.155720139