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Issue 24, 2016
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First total synthesis of trehalose containing tetrasaccharides from Mycobacterium smegmatis

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Abstract

Total synthesis of three important trehalose containing tetrasaccharides isolated from Mycobacterium smegmatis is reported for the first time, using regioselective opening of benzylidene acetals and stereoselective glycosylations as key steps. The 1,2-cis stereoselectivity in the glycosylation reactions was achieved using anchimeric assistance from a remote participating group, steric effects and solvent participation. The synthetic strategy can also be utilized for the assembly of structurally related oligosaccharides from M. tuberculosis.

Graphical abstract: First total synthesis of trehalose containing tetrasaccharides from Mycobacterium smegmatis

  • This article is part of the themed collection: New Talent
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Supplementary files

Article information


Submitted
22 Feb 2016
Accepted
24 Mar 2016
First published
24 Mar 2016

Org. Biomol. Chem., 2016,14, 5595-5598
Article type
Communication

First total synthesis of trehalose containing tetrasaccharides from Mycobacterium smegmatis

M. A. Chaube, V. A. Sarpe, S. Jana and S. S. Kulkarni, Org. Biomol. Chem., 2016, 14, 5595
DOI: 10.1039/C6OB00412A

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