title: Synthesis of a 3-Thiomannoside.
abstract: An efficient and straightforward synthesis of a novel 3-thiomannoside derivative (1,2,4,6-tetra-O-acetyl-3-S-acetyl-3-thio-β-d-mannopyranoside) was developed starting from levoglucosenone. A xanthate-thiocarbonate exchange under acidic conditions was the key step for the new C-S bond. The product was obtained enantiospecifically in very good overall yield.
authors.affiliation: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario - CONICET , Suipacha 531, S2002LRK, Rosario, Argentina.
authors.forename: María B
authors.initials: MB
authors.lastname: Comba
authors.affiliation: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario - CONICET , Suipacha 531, S2002LRK, Rosario, Argentina.
authors.forename: Alejandra G
authors.initials: AG
authors.lastname: Suárez
authors.affiliation: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario - CONICET , Suipacha 531, S2002LRK, Rosario, Argentina.
authors.forename: Ariel M
authors.initials: AM
authors.lastname: Sarotti
authors.affiliation: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario - CONICET , Suipacha 531, S2002LRK, Rosario, Argentina.
authors.forename: María I
authors.initials: MI
authors.lastname: Mangione
authors.affiliation: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario - CONICET , Suipacha 531, S2002LRK, Rosario, Argentina.
authors.forename: Rolando A
authors.initials: RA
authors.lastname: Spanevello
authors.affiliation: Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario - CONICET , Suipacha 531, S2002LRK, Rosario, Argentina.
authors.forename: Enrique D V
authors.initials: ED
authors.lastname: Giordano
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D008358:Mannose / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: C000610799:1,2,4,6-tetra-O-acetyl-3-S-acetyl-3-thio-beta-d-mannopyranoside; D008358:Mannose