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Expeditious Synthesis of Mycobacterium tuberculosis Sulfolipids SL-1 and Ac(2)SGL Analogues

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Field Value
 
Title Expeditious Synthesis of Mycobacterium tuberculosis Sulfolipids SL-1 and Ac(2)SGL Analogues
 
Creator SARPE, VA
KULKARNI, SS
 
Subject STRAIN H37RV
ACYL CHAINS
TREHALOSE
ANTIGENS
SULFATES
 
Description M. tuberculosis sulfoglycolipids SL-1 and Ac(2)SGL are highly immunogenic and potential vaccine candidates. A short and efficient methodology is reported for the synthesis of SL-1 and Ac(2)SGL analogues via regioselective functionalization of alpha,alpha-D-trehalose employing a highly regioselective late stage sulfation, as a key step. The SL-1 analogues 3a and 4 were obtained in 10 and 9 steps in 13.4% and 23.9% overall yields, respectively. The Ac(2)SGL analogue 5 was synthesized in 5 steps in 18.4% yield.
 
Publisher AMER CHEMICAL SOC
 
Date 2014-12-28T12:56:13Z
2014-12-28T12:56:13Z
2014
 
Type Article
 
Identifier ORGANIC LETTERS, 16(21)5732-5735
1523-7060
1523-7052
http://dx.doi.org/10.1021/ol5027987
http://dspace.library.iitb.ac.in/jspui/handle/100/16626
 
Language English