The Resolution and Absolute Stereochemistry of the Enantiomers of cis-1-[2-(Hydroxymethyl)-1,3-oxathiolan-5-yl)cytosine (BCH189): Equipotent Anti-HIV Agents

Abstract

Enzymic resolution of the monophosphate derivative of (/pm)-cis-1[2-(hydroxymethyl)-1, 3-oxathiolan-5-yl]cytosine using the 5′-nucleotidase from Crotalus atrox venom has allowed facile access to the individual enantimers. The absolute stereochemistry of the preferred (-)-enantiomer (8b) has been determined by X-ray crystallography of the bromine-contining derivative (10).