title: Synthesis of β-C-galactosyl D- and L-alanines.
abstract: Synthesis of β-C-D-galactosyl D- and L-alanines is carried out via a highly stereoselective Grignard reaction of glycosyl iodides, Sharpless dihydroxylation and S(N)2 displacement of the corresponding mesylate or tosylate. Alternatively, attempted triflation of the intermediate alcohols triggers a stereoselective debenzylative cyclization leading to interesting bicyclic trans-fused compounds.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Mumbai 400076, India.
authors.forename: V Narasimharao
authors.initials: VN
authors.lastname: Thota
authors.forename: Jacquelyn
authors.initials: J
authors.lastname: Gervay-Hague
authors.forename: Suvarn S
authors.initials: SS
authors.lastname: Kulkarni
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D005690:Galactose / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000409:Alanine; D005690:Galactose