A convenient synthesis of C-galactofuranosylic compounds (C-galactofuranosides)

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Title A convenient synthesis of C-galactofuranosylic compounds (C-galactofuranosides)
Author Owen, David J.; Thomson, Robin Joy; von Itzstein, Mark
Journal Name Carbohydrate Research
Year Published 2002
Place of publication UK
Publisher Pergamon
Abstract Galactofuranose sugar units are essential for the production of the cell coat of many pathogenic microorganisms. This sugar is not found in mammals, and so compounds that may interfere with the biosynthetic processing of this sugar unit provide interesting targets for drug design. This paper describes the use of a cyanation reaction for the production of a one-carbon extension of a galactofuranosylic unit at C-1, giving 2,5-anhydro-3,4,6,7-tetra-O-benzoyl--glycero--manno-heptononitrile. A procedure for the efficient hydrolysis of the introduced nitrile group to produce the methyl ester is reported, along with procedures for the synthesis of both the corresponding α,β-unsaturated, and 3-deoxy ester derivatives.
Peer Reviewed Yes
Published Yes
Publisher URI http://www.elsevier.com/wps/find/journaldescription.cws_home/424829/description#description
Alternative URI http://dx.doi.org/10.1016/S0008-6215(02)00133-7
Volume 337
Page from 2017
Page to 2022
ISSN 0008-6215
Date Accessioned 2003-03-25
Date Available 2009-10-19T05:22:20Z
Language en_AU
Research Centre Institute for Glycomics
Faculty Institute for Glycomics
Subject PRE2009-Organic Chemical Synthesis
URI http://hdl.handle.net/10072/6565
Publication Type Journal Articles (Refereed Article)
Publication Type Code c1

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