Synthesis of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino- and 1,6-Anhydro-2,3,4-trideoxy-3,4-epimino-β-D-hexopyranoses and Their NMR and Infrared Spectra
2004
Abstract
Synthesis and characterization of deoxy epimines derived from 1,6-anhydrohexopyranoses. A complete series of 2,3,4-trideoxy-2,3-epimino and 2,3,4-trideoxy-3,4-epimino derivatives of 1,6-anhydro-beta-D-hexopyranoses were prepared by lithium aluminum hydride reduction of vicinal trans azido tosylates.
Unusual formation of the aziridine ring from precursors with the trans-diequatorial arrangement of the reacting groups was observed. NMR and infrared spectra are discussed.