2,5-ANHYDRO-D-HEXITOLS: SYNTHESES OF 2,5-ANHYDRO-D-ALTRITOL AND 2,5-ANHYDRO-D-IDITOL

Article abstract of DOI:10.1016/0008-6215(84)85086-7

2,5-Anhydro-D-altritol (2a) and the previously-unknown 2,5-anhydro-D-iditol (3a) have been prepared from 2,5-anhydro-D-mannitol (1a).The preparation of 3a from the intermediate epoxide 7b is particularly sensitive to pH, and a mechanism is proposed to explain this.Attention is drawn to the limitations of the trifluoroperacetic acid-disodium hydrogenphosphate procedure for the epoxidation of alkenes of diminished reactivity.