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Please use this identifier to cite or link to this item: http://dspace.library.iitb.ac.in/jspui/handle/100/14240

Title: Rapid Transformation of D-Mannose into Orthogonally Protected D-Glucosamine and D-Galactosamine Thioglycosides
Authors: EMMADI, M
KULKARNI, SS
Keywords: ONE-POT PROTECTION
EFFICIENT SYNTHESIS
DERIVATIVES
OLIGOSACCHARIDES
SUGARS
ROUTE
AZIDE
1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE
REARRANGEMENT
SUBSTITUTION
Issue Date: 2011
Publisher: AMER CHEMICAL SOC
Citation: JOURNAL OF ORGANIC CHEMISTRY,76(11)4703-4709
Abstract: An expedient protocol for synthesis of orthogonally protected 2-azido-2-deoxy-D-glucosamine and 2-azido-2-deoxy-D-galactosamine donors from D-mannose is described. Readily available phenyl,beta-D-thiomannoside is rapidly transformed into D-GlcN(3) thioglycosides via a highly regioselective 3-O-acylation followed by 4,6-O-benzylidenation and azide displacement of C(2)-OTf, which is further converted into D-GalN(3) thioglycosides through Lattrell-Dax inversion of the C4 hydroxy group and its Boc protection. The reaction sequence may be completed in 2 days and involves simple workups and minimal column chromatography.
URI: http://dx.doi.org/10.1021/jo200342v
http://dspace.library.iitb.ac.in/jspui/handle/100/14240
ISSN: 0022-3263
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