ABSTRACT
Acylation of sugars is generally carried out with acyl chlorides or anhydrides, in pyridine solution, at room temperature. Allylation and benzylation is most efficiently achieved with the corresponding halides in anhydrous N,N-dimethylformamide, in the presence of a base, to generate the alcoholate. Sodium hydride is the most convenient one, but its use may
result in N-alkylation of acetamido sugars. Then benzylation may be achieved in the presence of a mixture of barium oxide and barium hydroxide octahydrate. In this way, benzyl 2-acetamido-3-0-benzyl-4,6-0-benzylidene-2-deoxy-a-n-glucopyranoside 1 was prepared in 87% yield in 15 min at room temperature [1].
