THE USE OF TETRAMETHYLGUANIDINIUM AZIDE IN NONHALOGENATED SOLVENTS AVOIDS POTENTIAL EXPLOSION HAZARDS

Authors
LI C SHIH TL JEONG JU ARASAPPAN A FUCHS PL
Citation
C. Li et al., THE USE OF TETRAMETHYLGUANIDINIUM AZIDE IN NONHALOGENATED SOLVENTS AVOIDS POTENTIAL EXPLOSION HAZARDS, Tetrahedron letters, 35(17), 1994, pp. 2645-2646
Citations number
6
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
17
Year of publication
1994
Pages
2645 - 2646
Database
ISI
SICI code
0040-4039(1994)35:17<2645:TUOTAI>2.0.ZU;2-S
Abstract
Tetramethylguanidinium azide was used in the quantitative conversion o f glycosyl halides 1 - 5 to the corresponding glycosyl azides 10 - 14. The stereoselective reactions occurred with complete inversion at the anomeric centers. The titled reagent was also employed in the selecti ve synthesis of pseudoglycosyl azide 16 and two steroidal azides 17 an d 18. All reactions were carried out in nonhalogenated solvents to avo id potential explosion hazards.