Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 11, Pages 4703-4709Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo200342v
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Funding
- Department of Science and Technology [SR/S1/OC-40/2009]
- Council of Scientific and Industrial Research [01(2376)/10/EMR-II]
- CSIR-New Delhi
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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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