Acetyl Migration in Partially Acetylated D-Glucopyrano-Sides and Acylamidohexopyranosides

Abstract

Abstract O-4-O-6 Acetyl migrations in partially O-acetylated 2- and 3-acylamidodeoxyhexopyranosides, including derivatives of kanamycin A, were found to be particularly suited to allow the regiospecific accessibility of their respective C-4 OH groups. Partially O-acetylated d-glucopyranosides, compared to the substrates above, showed slightly different aptitudes of migration. However, all O-4-O-6 migrations investigated proved to be irreversible under the conditions applied.