Y. Ishido, H. Komura, T. Yoshino
Dec 1, 1976
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Journal
Carbohydrate Research
Abstract
Abstract Fusion of 1,2;3,4-di- O -isopropylidene- d -mannitol 5,6-carbonate ( 1 ) with nitrogen heterocycles in the presence of catalytic amounts of tetraethylammonium bromide ( 9 ) and with p -toluenesulfonamide present gave the corresponding 1-deoxy- d -mannitol-1-yl derivatives in good yields. Under the same reaction conditions, 1,2,3,4-tetra- O -acetyl- d -mannitol 5,6-carbonate ( 26 ) gave a good yield of 2,3,5,6-tetra- O -acetyl-1,4-anhydro- d -mannitol ( 27 ). Treatment of 1 with benzoyl chloride and 9 afforded 2- O -benzoyl-1-chloro-1-deoxy-3,4;5,6-di- O -isopropylidene- d -mannitol ( 36 ) and with acid anhydrides the 1,2-di- O -acyl derivatives of di- O -isopropylidene- d -mannitol. The use of 3,4- O -isopropylidene- d -mannitol 1,2;5,6-dicarbonate ( 37 ) with benzoyl chloride and acid anhydrides in the presence of 9 gave corresponding products through reaction of both carbonate groups. The reaction mechanisms are discussed.