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Rapid Transformation of D-Mannose into Orthogonally Protected D-Glucosamine and D-Galactosamine Thioglycosides

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Field Value
 
Title Rapid Transformation of D-Mannose into Orthogonally Protected D-Glucosamine and D-Galactosamine Thioglycosides
 
Creator EMMADI, M
KULKARNI, SS
 
Subject 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
 
Description 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.
 
Publisher AMER CHEMICAL SOC
 
Date 2012-06-26T08:57:45Z
2012-06-26T08:57:45Z
2011
 
Type Article
 
Identifier JOURNAL OF ORGANIC CHEMISTRY,76(11)4703-4709
0022-3263
http://dx.doi.org/10.1021/jo200342v
http://dspace.library.iitb.ac.in/jspui/handle/100/14240
 
Language English