title: First total synthesis of trehalose containing tetrasaccharides from Mycobacterium smegmatis.
abstract: Total synthesis of three important trehalose containing tetrasaccharides isolated from Mycobacterium smegmatis is reported for the first time, using regioselective opening of benzylidene acetals and stereoselective glycosylations as key steps. The 1,2-cis stereoselectivity in the glycosylation reactions was achieved using anchimeric assistance from a remote participating group, steric effects and solvent participation. The synthetic strategy can also be utilized for the assembly of structurally related oligosaccharides from M. tuberculosis.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India. suvarn@chem.iitb.ac.in.
authors.forename: Manishkumar A
authors.initials: MA
authors.lastname: Chaube
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India. suvarn@chem.iitb.ac.in.
authors.forename: Vikram A
authors.initials: VA
authors.lastname: Sarpe
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India. suvarn@chem.iitb.ac.in.
authors.forename: Santanu
authors.initials: S
authors.lastname: Jana
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai-400076, India. suvarn@chem.iitb.ac.in.
authors.forename: Suvarn S
authors.initials: SS
authors.lastname: Kulkarni
mesh_terms: D002236:Carbohydrate Conformation; D020102:Mycobacterium smegmatis / Q000737:chemistry*; D009844:Oligosaccharides / Q000737:chemistry* / Q000302:isolation & purification; D014199:Trehalose / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009844:Oligosaccharides; D014199:Trehalose