Regioselective formation of 6-O-acylsucroses and 6,3'-di-O-acylsucroses via the stannylene acetal method.
Regioselective formation of 6-O-acylsucroses and 6,3'-di-O-acylsucroses in one pot with good yields was achieved for the first time by a typical acylation method of sucrose via its dibutylstannylene acetal. Pure monoesters at OH-6 and diesters at OH-6,3' obtained by these procedures were readily isolated by simple column chromatography, thus overcoming the main difficulties associated with regioselectivity, efficiency, and isolation techniques for the practical preparation. Explanations for the regioselectivities observed during this stannylene acetal-mediated reaction were also proposed based on the structures of the stannylene acetal in solution and the intramolecular migration of stannylenes.
Wang
Qinghui
Q
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012, PR China.
Zhang
Shufen
S
Yang
Jinzong
J
D000080:Acetals / Q000737:chemistry*; D002241:Carbohydrates / Q000737:chemistry; D002621:Chemistry / Q000379:methods; D002845:Chromatography / Q000379:methods; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D004952:Esters; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009947:Organotin Compounds / Q000737:chemistry; D013395:Sucrose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*
D000080:Acetals; D002241:Carbohydrates; D004952:Esters; D009947:Organotin Compounds; D013395:Sucrose; C031078:dibutyltin oxide