Synthesis and debenzoylation products of two perbenzoylated 2‐substituted 5‐ D ‐galactosyl‐1,3,4‐oxadiazoles

The synthesis of 2‐( p ‐chlorophenyl)‐5‐[1′,2′,3′,4′,5′‐penta‐ O ‐benzoyl‐ D ‐galactopentitol‐1‐yl]‐1,3,4‐oxadiazole is described. Its debenzoylation gave an equilibrium mixture of the 1,3,4‐oxadiazole derivative without protection of the hydroxyl group and the N ‐benzoyl‐ D ‐galactono‐1,4‐lactonehydrazone. A similar equilibrium was observed by debenzoylation of 2‐phenyl‐5‐[1′,2′,3′,4′,5′‐penta‐ O ‐benzoyl‐ D ‐galactopentitol‐1‐yl]‐1,3,4‐oxadiazole. The 1 H, 13 C nmr and ms spectra of these compounds are presented.