Issue 38, 2013

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

Abstract

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
06 Jul 2013
Accepted
12 Aug 2013
First published
14 Aug 2013

Org. Biomol. Chem., 2013,11, 6460-6465

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

V. A. Sarpe and S. S. Kulkarni, Org. Biomol. Chem., 2013, 11, 6460 DOI: 10.1039/C3OB41389F

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