Tetrahedron letters

One-pot inversion of D-mannono-1, 4-lactone for the practical synthesis of L-ribose

MJ Seo, J An, JH Shim, G Kim

Index: Seo, Myung Joon; An, Joungho; Shim, Jae Hak; Kim, Guncheol Tetrahedron Letters, 2003 , vol. 44, # 15 p. 3051 - 3052

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Citation Number: 18

Abstract

l-Ribose was synthesized in a concise manner from d-mannono-1, 4-lactone using one-pot inversion conditions. Treatment of d-mannono-1, 4-lactone with piperidine, followed by mesylation-induced SN2-type O-alkylation, afforded the desired one-pot inversion in an optimum yield, and the following straightforward transformations provided l-ribose in good yields.