Derivatives of D-Glucosamic Acid

Walden Inversion on the Fifth Carbon Atom

抄録

Ethyl 2-benzamido-4, 6-O-benzylidene-5-O-tosyl-2-deoxy-D-gluconate (III) was prepared from D-glucosamic acid. When treated with sodium acetate tosyloxy group on the fifth carbon of (III) was split off accompanying with a Walden inversion, and 2-benzamido-4, 6-Obenzylidene-2-dcoxy-2, 3-L-idoseenic 1, 5-lactone (IVa) was obtained. Since the tosyloxy group has no effective neighboring group for the inversion, its elimination was supposed to take place on the influence of carbonyl group of ester at δ-position, giving the lactone.