Sodium Salt of D-Glucono-1,5-lactone Tosylhydrazone: A Ready Access to a New Glucosylidene Carbene Precursor

László Somsák; Jean-Pierre Praly; Gérard Descotes

doi:10.1055/s-1992-21284

Synlett 1992; 1992(2): 119-120
DOI: 10.1055/s-1992-21284

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Sodium Salt of D-Glucono-1,5-lactone Tosylhydrazone: A Ready Access to a New Glucosylidene Carbene Precursor

László Somsák^* , Jean-Pierre Praly, Gérard Descotes

^*Université Claude Bernard Lyon I, Laboratoire de Chimie Organique II, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France

Abstract

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The sodium salt of 2,3,4,6-tetra-O-benzyl-D-glucono-1,5-lactone tosylhydrazone 4 has been prepared in two steps from 2,3,4,6-tetra-O-benzyl-D-glucopyranose (1). The possibility of using this salt as a glucosylidene carbene precursor has been demonstrated by synthesizing glucosylidene-spirocyclopropanes (2,3,4,6-tetra-O-benzyI-2′(or 3′)-cyano-1-deoxyspiro(D-glucose-1,1′-cyclopropanes]) via photolysis of 4 with acrylonitrile.

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