title: 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.
authors: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India. suvarn@chem.iitb.ac.in.
authors: Vikram A
authors: VA
authors: Sarpe
authors: Suvarn S
authors: SS
authors: Kulkarni
mesh_terms: D000080:Acetals / Q000737:chemistry*; D001597:Benzylidene Compounds / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014199:Trehalose / Q000737:chemistry*
chemical_list: D000080:Acetals; D001597:Benzylidene Compounds; D009942:Organometallic Compounds; D014199:Trehalose; C035719:diisobutylaluminum