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Synthesis 1996; 1996(5): 577-579
DOI: 10.1055/s-1996-4264
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Synthesis of Protected Glycopyranosylidene 1,1-Diazides

Jean-Pierre Praly* , Fabien Péquery, Carméla Di Stèfano, Gérard Descotes
  • *Laboratoire de Chimie Organique II associé au CNRS, Université Claude-Bernard Lyon I, CPE-ESCIL, 43 Boulevard du 11 Novembre 1918, F-69622 Villeurbanne, France
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Publikationsdatum:
31. Dezember 2000 (online)

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Treatment of peracetylated 1-bromo-β-D-glycopyranosyl chlorides with sodium azide in DMSO or, better, under PTC conditions, led to the corresponding glycopyranosylidene 1,1-diazides, in fair to excellent yield. Tetra-O-benzyl-D-glucono-1,5-lactone was converted into the corresponding diazide in 57% yield on treatment with trimethylsilyl azide in the presence of boron trifluoride-diethyl ether complex.

A protected glucono lactone and sugar 1,1-dihalides led efficiently to glycopyranosylidene 1,1-diazides