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Synlett 1994; 1994(5): 330-332
DOI: 10.1055/s-1994-22842
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C(5)-Epimerization in Glycopyranosides during the Cyclization of anomeric Radicals: Ease of the intramolecular 1,5-Hydrogen Atom Transfer

Alain De Mesmaeker* , Adrian Waldner, Pascale Hoffmann, Tammo Winkler
  • *Central Research Laboratories, Ciba-Geigy Ltd., CH-4002 Basel, Switzerland.
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Publication Date:
22 March 2002 (online)

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The extent and the regioselectivity of the intramolecular 1,5-hydrogen atom transfer in glycopyranosidic radicals have been studied by deuteration experiments with n-Bu3SnD. Exclusive translocation of the primary cyclized radical 4 to the C(5)-center (in 6) has been observed. Conformational effects are, most probably, governing the ease of the intramolecular hydrogen atom transfer.