C(5)-Epimerization in Glycopyranosides during the Cyclization of anomeric Radicals: Ease of the intramolecular 1,5-Hydrogen Atom Transfer
- 1 January 1994
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1994 (05) , 330-332
- https://doi.org/10.1055/s-1994-22842
Abstract
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.Keywords
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