N-Benzhydryl-2,5-anhydro-2,5-imino-D-glucitol → (1S,2S,3S,4R)-1,4-bis(hydroxymethyl)-5-oxa-6-azabicyclo[2.1.1]hexane-2,3-diol

Participants

Reaction Steps

A mixture of N-benzhydryl-2,5-anhydro-2,5-imino-D-glucitol (Formula XI, R3 =Ph2CH 8.40 g, 25.5 mmol) and 0.42 g of 20% PD(OH)2 /carbon in 100 mL of MeOH was set shaking on a Parr apparatus under 60 psig of hydrogen overnight. This solution was then filtered and concentrated. Hexane (ca. 300 mi) was added, and the solvent was then removed from a white solid, which was washed with ca. 200 mL of hexane. The product was recrystallized from ETOH/CH3CN to give 3.79 g (91%) of white needles, mp 139°-142.50° C. (corrected). Both 1H and 13C NMR in D2O supported the assigned structure.

Provenance & Evidence