Carbon Dioxide → HCID 178521060, compound

Participants

Reaction Steps

A solution of 25 mg. of 6,7-dihydro-3-[3,5-di-O-(p-toluoyl)-60 ,β-D-erythro-pentofuranosyl]imidazo[4,5-d][1,3]diazepin-8(3H)-one in 5 ml. of ethanol is treated with 10 mg. of sodium borohydride and stirred at room temperature for 15 minutes. About 5 mg. of sodium is then added, the solution is stirred at room temperature for 15 minutes, then neutralized with carbon dioxide. The mixture is evaporated at reduced pressure and the residue is partitioned between 10 ml. of ether and 10 ml. of water. The aqueous phase is separated and evaporated at reduced pressure. The residue is applied to the top of a 1 × 10 cm. column of Dowex 50×2 resin (a strongly acidic cation exchange resin) in the ammonium form. The resin is eluted with 25 ml. of 0.01N aqueous ammonia and the eluate is evaporated at reduced pressure to give a residue consisting of a mixture of the four possible isomers, one of which is (R)-3-(2-deoxy-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (pentostatin).

Provenance & Evidence