Open AccessSynthesis of N-pentofuranosyl oxazolines and amides though the selective transformations of D-sugar acetonides
Author(s) -
Grigorii G. Sivets,
A. V. Sivets
Publication year - 2021
Publication title -
doklady nacionalʹnoj akademii nauk belarusi
Language(s) - English
Resource type - Journals
eISSN - 2524-2431
pISSN - 1561-8323
DOI - 10.29235/1561-8323-2021-65-5-558-567
Subject(s) - chemistry , acetonitrile , hydrolysis , boron trifluoride , glycosyl , organic chemistry , medicinal chemistry , lewis acids and bases , xylose , acetamide , catalysis , fermentation
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.