NUCLEOPHILE INDUCED REARRANGEMENTS OF THIOGLYCOSIDES - FORMATION OF 6-THIO GLYCOSIDES AND 1,6-THIOANHYDROSUGARS

Authors
LOWARY TL BUNDLE DR
Citation
Tl. Lowary et Dr. Bundle, NUCLEOPHILE INDUCED REARRANGEMENTS OF THIOGLYCOSIDES - FORMATION OF 6-THIO GLYCOSIDES AND 1,6-THIOANHYDROSUGARS, Tetrahedron : asymmetry, 5(12), 1994, pp. 2397-2404
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
12
Year of publication
1994
Pages
2397 - 2404
Database
ISI
SICI code
0957-4166(1994)5:12<2397:NIROT->2.0.ZU;2-#
Abstract
Treatment of Ethyl 2,3 di-O-toluenesulfonyl-1-thio-beta-D-glucopyranos ide 12 with sodium methoxide at low temperature gives Methyl 3,4 anhyr o-6-S-ethyl-beta-D-galactopyranoside 13, whereas treatment with sodium iodide in reluxing butanone yields 2,3 di-O-benzoyl-4-O-toluensesulfo nyl-1,6 thioanhydro-D-glucopyranose 19.