Acyl chloride/DABCO-promoted acetal migration of 1,2:4,5-di-O-isopropylidene-D-fructopyranose.
An unprecedented acetal migration was observed when 1,2:4,5-di-O-isopropylidene-D-fructose was treated with various acyl chlorides and 1,4-diaza-bicyclo[2.2.2]octane (DABCO). 2,3:4,5-Di-O-isopropylidene-D-fructose derivatives were isolated as the only product in high to quantitative yields. The acylium cations generated in situ were speculated as the electrophilic species to initiate the migration process.
Meng
Xiang-Bao
XB
Department of Chemical Biology, School of Pharmaceutical Sciences, State Key Laboratory of Natural and Biomimetic Drugs, Peking University Health Science Center, Beijing 100083, PR China.
Li
Yun-Feng
YF
Li
Zhong-Jun
ZJ
D000215:Acylation; D000475:Alkenes / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002712:Chlorides; D005632:Fructose / Q000031:analogs & derivatives / Q000737:chemistry*; D008958:Models, Molecular; D010879:Piperazines
D000475:Alkenes; D002712:Chlorides; D010879:Piperazines; D005632:Fructose; C013658:propylene; C007306:triethylenediamine