Synthesis of a 3-Thiomannoside
María B Comba1, Alejandra G Suárez1, Ariel M Sarotti1
1Instituto de Química Rosario, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario - CONICET , Suipacha 531, S2002LRK, Rosario, Argentina.
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.
Related Concept Videos
Oligosaccharide Assembly
Multiple sugar molecules that may or may...
Preparation and Reactions of Sulfides
Preparation and Reactions of Thiols
Biosynthesis of Polysaccharides
Alkylation of β-Diester Enolates: Malonic Ester Synthesis


