Synthesis of N-pentofuranosyl oxazolines and amides though the selective transformations of D-sugar acetonides
https://doi.org/10.29235/1561-8323-2021-65-5-558-567
Abstract
The method for synthesis of N-pentofuranosyl oxazolines was developed from the protected 1,2-O-acetonides of D-xylofuranose, -ribofuranose, and -arabinofuranose using boron trifluoride diethyl etherate, acetonitrile, and potassium hydrogen difluoride. A possible mechanism of the catalyzed reaction of acylated acetonides with acetonitrile in the presence of Lewis acid was considered in terms of the activation and cleavage of the 1,3-dioxalane part of the xylose derivative fol- lowed by the conversions of intermediates to α-isooxazoline. The hydrolysis reactions of N-α-glycosyl oxazolines were stud- ied in the acidic and neutral conditions. N-α-xylofuranosyl acetamide derivatives were prepared in high yields as a result of selective hydrolysis of protected α-xylofuranosyl isooxazolines in the neutral conditions.
About the Authors
G. G. Sivets
Институт биоорганической химии Национальной академии наук Беларуси
Belarus
Belarus
Sivets Grigorii G. – D. Sc. (Chemistry), Head of the Laboratory
5/2, Kuprevich Str., 220141, Minsk
A. V. Sivets
Институт биоорганической химии Национальной академии наук Беларуси
Belarus
Belarus
Sivets Aleksey V. – Postgraduate student
5/2, Kuprevich Str., 220141, Minsk
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