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
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Creator |
SARPE, VA
KULKARNI, SS |
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Subject |
DIACYLTREHALOSE GLYCOLIPIDS
MYCOBACTERIUM-TUBERCULOSIS CAENORHABDITIS-ELEGANS BIOLOGICAL-ACTIVITIES ANALOGS OLIGOSACCHARIDES DERIVATIVES CLEAVAGE CYCLOTREHALANS MARADOLIPIDS |
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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.
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Publisher |
ROYAL SOC CHEMISTRY
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Date |
2014-10-15T10:22:21Z
2014-10-15T10:22:21Z 2013 |
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Type |
Article
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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 |
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Language |
en
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