NEW AND CONVENIENT SYNTHESIS OF 2-DEOXY-D-RIBOSE FROM 2,4-O-ETHYLIDENE-D-ERYTHROSE

A new synthesis is described of 2-deoxy-D-erythro-pentose [2-deoxy-D-ribose, 2-deoxy-D-arabinose (1)], starting from D-glucose. The synthesis proceeds through direct olefination of 2, 4-O-ethylidene-D-erythrose (2) by addition of the stabilized ylides generated from dimethylphosphorylmethyl phenyl sulfide (4) and the corresponding sulfoxide 5. These afford the key intermediates, thio-enol ether 7 and α, β-unsaturated sulfoxide 8, which when subjected to mercuric ion assisted hydrolysis gave high yields of 2-deoxy-D-ribose (1). This facile chain extension of 2 required its existence as a monomer, and conditions effective for obtaining the monomer have been developed. Detailed and 13C NMR studies of these compounds are presented. © 1979, American Chemical Society. All rights reserved.