Synthesis of some 2-alkoxy glyco-[2,1-d]-2-oxazolines and evaluation of their glycosylation reactivity

Synthesis of some 2-alkoxy glyco-[2,1-d]-2-oxazolines and evaluation of their glycosylation reactivity Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2012, Volume: 356, Pages: 172-179 Pages count : 8 DOI: 10.1016/j.carres.2012.03.026

Authors

Pertel Sergey S. ¹ , Kononov Leonid O. ² , Zinin Alexander I. ² , Chirva Vasily Ja. ¹ , Kakayan Elena S. ¹

Affiliations

1	Department of Organic and Biological Chemistry, V.I. Vernadsky Taurida National University, Vernadsky ave. 4, 95007 Simferopol, Crimea, Ukraine.
2	N.D.Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp. 47, 119991 Moscow, Russian Federation,

The synthesis of the title compounds using intramolecular nucleophilic substitution reactions in the molecules of the corresponding 2-alkoxycarbonylamino-2-deoxy glucosyl halides was studied. It was found that in contrast to the 2-alkyl (aryl) glyco-[2,1-d]-2-oxazolines, the synthesis of the target 2-alkoxy glyco-[2,1-d]-2-oxazolines was possible only in highly basic media. The synthesized 2-alkoxy oxazoline derivatives turned out to be active glycosyl donors and were used for stereoselective 1,2-trans glycosylation reactions catalyzed by weak protic acid under very mild conditions, thus preventing anomerization and other side reactions. As a result of this glycosylation, the glycoside and oligosaccharide derivatives containing urethane N-protecting groups were formed.

Pertel S.S. , Kononov L.O. , Zinin A.I. , Chirva V.J. , Kakayan E.S.
Synthesis of some 2-alkoxy glyco-[2,1-d]-2-oxazolines and evaluation of their glycosylation reactivity
Carbohydrate Research. 2012. V.356. P.172-179. DOI: 10.1016/j.carres.2012.03.026 WOS Scopus OpenAlex

Web of science:	WOS:000305338000017
Scopus:	2-s2.0-84862316106
OpenAlex:	W2038483157

DB	Citing
OpenAlex	13
Scopus	14
Web of science	14