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Synthesis and debenzoylation products of two perbenzoylated 2‐substituted 5‐ D ‐galactosyl‐1,3,4‐oxadiazoles
Author(s) -
Cannizzaro Carina E.,
Thiel Inge M. E.,
D'Accorso Norma B.
Publication year - 1998
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570350238
Subject(s) - chemistry , derivative (finance) , oxadiazole , medicinal chemistry , organic chemistry , economics , financial economics
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.