An improved route to 1,2-dideoxy-beta-1-phenyl-D-ribofuranose

An efficient synthesis of the aryl nucleoside analogue 1,2-dideoxy-beta-1-phenyl-D-ribofuranose (1) is described. This route utilizes the addition of phenyllithium to a protected 2-deoxyribonolactone followed by reduction with triethylsilane/boron trifluoride etherate to selectively produce the beta-anomer. Deprotection yields the desired aryl C-nucleoside in 27% overall yield from 2-deoxy-D-ribose.