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Synthesis 1991; 1991(10): 885-888
DOI: 10.1055/s-1991-26601
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Reaktionen mit und in wasserfreiem Fluorwasserstoft 7.1 Von Isopropylidenzuckern zu acylierten Pyranosyl- oder Furanosylfluoriden in einem Schritt

Ralf Miethchen* , Torsten Gabriel, Gundula Kolp
  • *Lehrstuhl für Organische Chemie der Universität Rostock, Buchbinderstraße 9, D-(O)-2500 Rostock 1, Germany
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Publication Date:
29 April 2002 (online)

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Reactions with and in Anhydrous Hydrogen Fluoride 7.1 From Isopropylidene Sugars to Acylated Pyranosyl and Furanosyl Fluorides in One Step A convenient one-pot transformation of the 6-O-substituted 1,2:3,4-di-O-isopropylidene-α-D-galactopyranoses 1a-g and the 3-O-substituted 1,2:5,6-di-O-isopropylidene-α-D-glucofuranoses 5a-c is described to form the corresponding 6-O-substituted 2,3, 4-tri-O-acyl-α-D-galactopyranosyl fluorides 2a-f, 3e, 3g and 3-O-substituted 2,5,6-tri-O-acetyl-α/β-D-glucofuranosyl fluorides 6a-c, respectively. This short way of synthesis is possible by use of the new homogeneous reagent/catalyst/solvent combination composed of anhydrous hydrogen fluoride/nitromethane/carboxylic acid anhydride (2: 5:1-1.5). A ring contraction or extension is not found; in addition the functional groups are regiostable in 6-position of 2a-f, 3e, 3g and in 3-position of 6a-c, respectively.