SYNTHESIS AND HIV INHIBITION-ACTIVITY OF 2',3'-DIDEOXY-3'-C-HYDROXYMETHYL NUCLEOSIDES

A series if 2',3'-dideoxy-3'-C-hydroxymethyl purine nucleosides were p repared based on the photo chemical ring expansion of a chiral cyclobu tanone precursor, S)-trans-2,3-bis[(benzoyloxy)methyl]cyclobutanone, i n the presence of a B-substituted purine. Both alpha- and beta-anomers are produced in this transformation. Deprotection was effected by rea ction of the photoadducts with saturated methanolic ammonia. Nine puri ne nucleosides were tested for their inhibitory effect of HIV IIIB vir us on H9 cells. The 6-hexyloxy and adenine derivatives 4e,c, respectiv ely, appeared to be most effective at inhibiting viral reproduction wi th 4e comparable in activity to ddI and AZT.