The Journal of Organic Chemistry

A new and convenient synthesis of 2-deoxy-D-ribose from 2, 4-O-ethylidene-D-erythrose

JR Hauske, H Rapoport

Index: Hauske,J.R.; Rapoport,H. Journal of Organic Chemistry, 1979 , vol. 44, # 14 p. 2472 - 2476

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Citation Number: 22

Abstract

A new synthesis is described of 2-deoxy-D-erythro-pentose [2-deoxy-~-ribose, 2-deoxy-~- arabinose (111, starting from D-glucose. The synthesis proceeds through direct olefination of 2, 4-O-ethylidene-~-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 cr, p-unsaturated sulfoxide 8, which ...