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Desymmetrization of trehalose via regioselective DIBAL reductive ring opening of benzylidene and substituted benzylidene acetals

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Title Desymmetrization of trehalose via regioselective DIBAL reductive ring opening of benzylidene and substituted benzylidene acetals
 
Creator SARPE, VA
KULKARNI, SS
 
Subject DIACYLTREHALOSE GLYCOLIPIDS
MYCOBACTERIUM-TUBERCULOSIS
CAENORHABDITIS-ELEGANS
BIOLOGICAL-ACTIVITIES
ANALOGS
OLIGOSACCHARIDES
DERIVATIVES
CLEAVAGE
CYCLOTREHALANS
MARADOLIPIDS
 
Description Trehalose dibenzylidene and substituted dibenzylidene acetals were reductively opened either at O6 or O4 in a regioselective manner by using a DIBAL stock solution prepared in toluene or dichloromethane, respectively, to achieve desymmetrization of the trehalose core. The method was applied to synthesize various biologically important unsymmetrically substituted trehalose glycoconjugates, including a mycobacterial trisaccharide, a 4-epi-trehalosamine analog and a maradolipid.
 
Publisher ROYAL SOC CHEMISTRY
 
Date 2014-10-15T10:22:21Z
2014-10-15T10:22:21Z
2013
 
Type Article
 
Identifier ORGANIC & BIOMOLECULAR CHEMISTRY, 11(38)6460-6465
1477-0520
1477-0539
http://dx.doi.org/10.1039/c3ob41389f
http://dspace.library.iitb.ac.in/jspui/handle/100/14734
 
Language en