Stereoselective synthesis of a ketohexofuranose from an aldohexopyranose by a [6+1-1] strategy.
Ozonolysis of 2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hex-1-enitol gave 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-2-ulose (5). Subsequent hydrolysis and acetylation of 5 provided 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-D-fructofuranose 6 in excellent yield. This methodology allows specific deuteration at C-1 of a protected D-fructofuranose derivative. This approach therefore could serve as [6+1-1] formulation for hexose series inter-conversion, that is, aldohexopyranose to ketohexofuranose.
Babu
Boga Sobhana
BS
Department of Chemistry, Indian Institute of Technology, Madras, Chennai 600 036, India.
Balasubramanian
Kalpattu Kuppuswamy
KK
D000107:Acetylation; D001089:Arabinose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D002236:Carbohydrate Conformation; D003903:Deuterium; D006601:Hexoses / Q000138:chemical synthesis; D006868:Hydrolysis; D007661:Ketoses / Q000138:chemical synthesis; D015394:Molecular Structure; D010126:Ozone / Q000737:chemistry
D006601:Hexoses; D007661:Ketoses; D010126:Ozone; D003903:Deuterium; D001089:Arabinose