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.
Wang
Qingbing
Q
Department of Chemistry, East China Normal University, Shanghai 200062, China.
Fu
Jie
J
Zhang
Jianbo
J
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