BASE-INDUCED RING-OPENING OF A SUGAR DERIVATIVE O-CARBAMATE

Authors
TAMION R MARSAIS F QUEGUINER G
Citation
R. Tamion et al., BASE-INDUCED RING-OPENING OF A SUGAR DERIVATIVE O-CARBAMATE, Tetrahedron letters, 36(16), 1995, pp. 2761-2764
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
16
Year of publication
1995
Pages
2761 - 2764
Database
ISI
SICI code
0040-4039(1995)36:16<2761:BROASD>2.0.ZU;2-V
Abstract
Treatment of the N,N-diisopropylcarbamate of the isosorbide exo monome thyl ether with n-butyllithium at low temperature induced the opening of the ring bearing the carbamate moiety. The observed rearrangement l ed to the corresponding enol carbamate of 3R,4S)-2-acetyl-3-hydroxy-4- methoxytetrahydrofuran in good yield.