A facile preparation of peracylated alpha-aldopyranosyl chlorides with thionyl chloride and tin tetrachloride.
Aldopyranose peracetates react with thionyl chloride and tin tetrachloride, producing the corresponding peracylated aldopyranosyl chlorides in very good to excellent yields (88-100%) with exclusive alpha-anomeric selectivity and short reaction times. The use of peracylated sugars as the substrate in large scale reactions also proceeds in high yield.
Department of Chemistry, East China Normal University, Shanghai 200062, China.
Qingbing
Q
Wang
Jie
J
Fu
Jianbo
J
Zhang
D000215:Acylation; D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013461:Sulfur Oxides; D017971:Tin Compounds
D004187:Disaccharides; D009844:Oligosaccharides; D010880:Piperidines; D013461:Sulfur Oxides; D017971:Tin Compounds; C023589:thionyl chloride; C041694:stannic chloride