A novel free C-12 higher carbon sugar: asymmetric synthesis and reactivity with nucleophiles

Abstract

A novel C-12 higher carbon sugar, (1 R)-(1,4:3,6-dianhydro- d-mannitol-2-yl)-1,4:3,6-dianhydro- d-fructose, was firstly synthesized via a convenient aldol reaction of 1,4:3,6-dianhydro- d-fructose without any protection and activation of functional groups. The reactivity of the novel higher sugar with nucleophiles was also studied, through which a series of oxazolidines and other derivatives of the higher sugar were available. The study showed that the higher sugar possesses a highly reactive carbonyl group and a good stereo controlling ability in the reaction.