danДоклады Национальной академии наук БеларусиDoklady of the National Academy of Sciences of Belarus1561-83232524-2431The Republican Unitary Enterprise Publishing House "Belaruskaya Navuka"10.29235/1561-8323-2021-65-5-558-567dan-1005Research ArticleХИМИЯCHEMISTRYСинтез N-пентофуранозилоксазолинов и амидов через селективные трансформации ацетонидов D-сахаровSynthesis of N-pentofuranosyl oxazolines and amides though the selective transformations of D-sugar acetonidesСивецГ. Г.SivetsG. G.

Сивец Григорий Гаврилович – д-р хим. наук, за ведующий лабораторией

ул. Купревича, 5/2, 220141, Минск

Sivets Grigorii G. – D. Sc. (Chemistry), Head of the Laboratory

5/2, Kuprevich Str., 220141, Minsk

sivets@iboch.byСивецА. В.SivetsA. V.

Сивец Алексей Васильевич – аспирант

ул. Купревича, 5/2, 220141, Минск

Sivets Aleksey V. – Postgraduate student

5/2, Kuprevich Str., 220141, Minsk

alsiv@iboch.byИнститут биоорганической химии Национальной академии наук БеларусиИнститут биоорганической химии Национальной академии наук Беларуси202107112021655558–567Copyright © Сивец Г.Г., Сивец А.В., 20212021Сивец Г.Г., Сивец А.В.Sivets G.G., Sivets A.V.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://doklady.belnauka.by/jour/article/view/1005

Метод синтеза N-гликозилоксазолинов разработан из блокированных 1,2-О-ацетонидов D-ксилофуранозы, -рибофуранозы и -арабинофуранозы с использованием ацетонитрила, эфирата трехфтористого бора и гидрофторида калия. Возможный механизм реакции 3,5-ди-О-бензоилированных ацетонидов пентофураноз с ацетонитрилом в присутствии кислоты Льюиса в качестве катализатора рассмотрен через активацию, раскрытие 1,3-диоксаланового фрагмента производного ксилофуранозы и последующие превращения интермедиатов в α-изооксазолин. Реакции гидролиза N-α-гликозилоксазолинов изучены в кислых и нейтральных условиях. В результате селективного гидролиза блокированных α-ксилофуранозилизооксазолинов в нейтральных условиях были получены производные N-α-ксилофуранозилацетамида с высокими выходами. 

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.

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The authors declare that there are no conflicts of interest present.