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

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Madhu Emmadi and Suvarn S. Kulkarni*

Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India

J. Org. Chem., 2011, 76 (11), pp 4703–4709

DOI: 10.1021/jo200342v

Publication Date (Web): April 21, 2011

*E-mail: suvarn@chem.iitb.ac.in.

Section:

Carbohydrates

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 β-d-thiomannoside is rapidly transformed into d-GlcN₃ thioglycosides via a highly regioselective 3-O-acylation followed by 4,6-O-benzylidenation and azide displacement of C2-OTf, which is further converted into d-GalN₃ 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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History

Published In Issue June 03, 2011
Article ASAPMay 03, 2011
Just Accepted ManuscriptApril 21, 2011
Received: February 25, 2011

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

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Synthesis of Maradolipid

Study of the Stereoselectivity of 2-Azido-2-deoxygalactosyl Donors: Remote Protecting Group Effects and Temperature Dependency

Design and Synthesis of Unnatural Heparosan and Chondroitin Building Blocks

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