C(5)-EPIMERIZATION IN GLYCOPYRANOSIDES DURING THE CYCLIZATION OF ANOMERIC RADICALS - EASE OF THE INTRAMOLECULAR 1,5-HYDROGEN ATOM-TRANSFER

Authors
DEMESMAEKER A WALDNER A HOFFMANN P WINKLER T
Citation
A. Demesmaeker et al., C(5)-EPIMERIZATION IN GLYCOPYRANOSIDES DURING THE CYCLIZATION OF ANOMERIC RADICALS - EASE OF THE INTRAMOLECULAR 1,5-HYDROGEN ATOM-TRANSFER, Synlett, (5), 1994, pp. 330-332
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
5
Year of publication
1994
Pages
330 - 332
Database
ISI
SICI code
0936-5214(1994):5<330:CIGDTC>2.0.ZU;2-0
Abstract
The extent and the regioselectivity of the intramolecular 1,5-hydrogen atom transfer in glycopyranosidic radicals have been studied by deute ration experiments with n-Bu3SnD. Exclusive translocation of the prima ry cyclized radical 4 to the C(5)-center (in 6) has been observed. Con formational effects are, most probably, governing the ease of the intr amolecular hydrogen atom transfer.