Potential Anticancer Agents. 1 LIV. Synthesis of 3-Amino-2, 3-dideoxy-β-D-ribofuranosides via the 2, 3-Episulfonium Ion Approach

CD Anderson, WW Lee, L Goodman…

Index: Anderson,C.D. et al. Journal of the American Chemical Society, 1961 , vol. 83, p. 1900 - 1906

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Citation Number: 14

Abstract

Application of a synthetic sequence involving migration of an ethylthio group z~ ia an episulfonium intermediate led to a synthesis of 3-amino-2, 3-dideoxy-~-ribose isolated as its hydrochloride XVII. The 3-ethylthio glycoside I was converted to its 5-0-trityl derivative V, then treated with methanesulfonyl chloride to give the chloroglycoside VIII. Azidolysis of the chloro compound VI11 gave the mixture of azides IX which was reduced to the amine ...