ENANTIOSPECIFIC SYNTHESIS OF THE IMMUNOPOTENTIATORS erythro-9 (2-HYDROXY-3-NONYL) HYPOXANTHINES AND THE threo-DIASTEREOMERS.

Article abstract of DOI:10.1016/S0040-4039(01)81715-9

The title compounds were prepared enantiospecifically by kinetic resolution of (+/-) 1-nonene-3-ol via Sharpless oxidation.The products 1,2R-epoxy-nonane-3S-ol and 1-nonene-3R-ol were efficiently converted to all four stereoisomers of 2-hydroxy-3-nonylamine, which were subsequently incorporated into the target hypoxanthines to evaluate their immunopotentiating activity.