Article
One-pot Synthesis of N-glycooxazolines, N-glycoaminooxazolines, and N-glycothiazolines From Glycals
European Journal of Organic Chemistry
(2012)
Abstract
Novel one-pot syntheses of N-glycooxazolines (N at C-1), N-glycoaminooxazolines, and N-glycothiazolines have been developed. Thus, the reaction of tri-O-benzyl-D-glucal or tri-O-benzyl-D-galactal with aryl amides, heteroaryl amides, thioamides, and substituted ureas in the presence of N-iodosuccinimide (NIS) in dry propionitrile at 45 °C afforded the cyclized products in good yields. When tris(O-tert-butyldimethylsilyl)-D-glucal was employed, the 2-deoxy-2-iodoglycosylamide was isolated instead. Treatment of this newly formed glycosylamide with an anhydrous base afforded the O-glycooxazoline (O at C-1) in high to moderate yields. Product outcomes and the overall stereoselectivity of the reactions were found to be highly dependent on the nature of the sugar protecting group, the nature of the substituent on the amide, and the reaction temperature.
Keywords
- Carbohydrates,
- Heterocycles,
- Natural products,
- Synthetic methods
Disciplines
Publication Date
June, 2012
DOI
10.1002/ejoc.201200130
Citation Information
Cecilia Marzabadi, Erica M. Reid, Edward S. Vigneau, Synthia S. Gratia, et al.. "One-pot Synthesis of N-glycooxazolines, N-glycoaminooxazolines, and N-glycothiazolines From Glycals" European Journal of Organic Chemistry Vol. 2012 Iss. 17 (2012) p. 3295 - 3303 ISSN: 1434-193X Available at: http://works.bepress.com/cecilia_marzabadi/18/