SYNTHESIS AND SPECTROSCOPIC STUDIES OF ACETYLATED ALKYL 1-AZIDO-D-GLUCOPYRANOSIDES

Authors
PRALY JP DISTEFANO C BOUCHU MN ELKHARRAF Z FAURE R DESCOTES G
Citation
Jp. Praly et al., SYNTHESIS AND SPECTROSCOPIC STUDIES OF ACETYLATED ALKYL 1-AZIDO-D-GLUCOPYRANOSIDES, Tetrahedron, 49(43), 1993, pp. 9759-9766
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
43
Year of publication
1993
Pages
9759 - 9766
Database
ISI
SICI code
0040-4020(1993)49:43<9759:SASSOA>2.0.ZU;2-C
Abstract
On treatment with trimethylsilyl azide in the presence of boron triflu oride etherate, anomeric orthoesters undergo the exchange of one anome ric alkoxy group by an azido group to yield two epimeric mono azido de rivatives (approximately 85% total yield). It was observed that both l ateral N-15 nuclei in axially oriented azido groups are shielded as co mpared to their equatorial counterparts.