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Desymmetrization of trehalose via regioselective DIBAL reductive ring opening of benzylidene and substituted benzylidene acetals
- Source :
- IndraStra Global.
- Publication Year :
- 2013
- Publisher :
- ROYAL SOC CHEMISTRY, 2013.
-
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.
- Subjects :
- Oligosaccharides
Stereoisomerism
Ring (chemistry)
Benzylidene Compounds
Biochemistry
Desymmetrization
chemistry.chemical_compound
Acetals
Organometallic Compounds
Organic chemistry
Trisaccharide
Physical and Theoretical Chemistry
Dichloromethane
Cleavage
chemistry.chemical_classification
Maradolipids
Cyclotrehalans
Molecular Structure
Biological-Activities
Organic Chemistry
Trehalose
Regioselectivity
chemistry
Mycobacterium-Tuberculosis
Benzylidene compounds
Caenorhabditis-Elegans
Diacyltrehalose Glycolipids
Oxidation-Reduction
Derivatives
Analogs
Subjects
Details
- Language :
- English
- ISSN :
- 23813652
- Database :
- OpenAIRE
- Journal :
- IndraStra Global
- Accession number :
- edsair.doi.dedup.....33629fbd32e1389788e9bf5a7b5bc934