Towards complete stereochemical control: complementary methods for the synthesis of six diastereoisomeric monosaccharide mimetics

R Hodgson, T Majid, A Nelson

Index: Hodgson, Robert; Majidb, Tahir; Nelson, Adam Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 12 p. 1444 - 1454

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Citation Number: 19

Abstract

Complementary methods for the synthesis of diastereomeric monosaccharide mimetics are described which rely on the functionalisation of derivatives of 2-butyl-6-methoxy-2, 6- dihydropyran-3-one. The stereochemical outcome of dihydroxylation of these derivatives under Upjohn's and Donohoe's (directed) reaction conditions are described. The hydrolyses of diastereomeric 2-butyl-4, 5-epoxy-3-hydroxy-6-methoxytetrahydropyrans, generated ...