A PROTECTED FORM OF (1S,2R,3S,4R)-4-AMINOCYCLOPENTANE-1,2,3-TRIOL, A USEFUL PRECURSOR TO 5′-NOR CARBOCYCLIC NUCLEOSIDES

Abstract

5′-Nor carbocyclic nucleosides have been found to possess a variety of meaningful biological properties. One of the building blocks for this class of compounds is (1S,2R,3S,4R)-4-aminocyclopentane-1,2,3-triol. To date, the reported routes to this compound are not particularly facile. Thus, a convenient route to this triol in its protected isopropylidene form (2) from (+)-(1R,4S)-4-hydroxy-2-cyclopenten-1-yl acetate. This will facilitate the preparation of new 5′-nor carbocyclic nucleosides in the “D-ribo-like” configuration. This method is also adaptable to the “L-like” series and the 2′- and 3′-deoxy analogs.

ACKNOWLEDGMENT

This research was supported by funds from the Department of Health and Human Services (AI31718 and AI48495), which is appreciated.