Rapid Transformation of D-Mannose into Orthogonally Protected D-Glucosamine and D-Galactosamine Thioglycosides
DSpace at IIT Bombay
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Title |
Rapid Transformation of D-Mannose into Orthogonally Protected D-Glucosamine and D-Galactosamine Thioglycosides
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Creator |
EMMADI, M
KULKARNI, SS |
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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 |
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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.
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Publisher |
AMER CHEMICAL SOC
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Date |
2012-06-26T08:57:45Z
2012-06-26T08:57:45Z 2011 |
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Type |
Article
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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 |
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Language |
English
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