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Synthesis of some 2-alkoxy glyco-[2,1-d]-2-oxazolines and evaluation of their glycosylation reactivity.
Carbohydr Res. 2012 Jul 15; 356:172-9.CR

Abstract

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.

Authors+Show Affiliations

Department of Organic and Biological Chemistry, V.I. Vernadsky Taurida National University, Vernadsky ave. 4, 95007 Simferopol, Crimea, Ukraine. orgchem@crimea.eduNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

22521206

Citation

Pertel, Sergey S., et al. "Synthesis of some 2-alkoxy Glyco-[2,1-d]-2-oxazolines and Evaluation of Their Glycosylation Reactivity." Carbohydrate Research, vol. 356, 2012, pp. 172-9.
Pertel SS, Kononov LO, Zinin AI, et al. Synthesis of some 2-alkoxy glyco-[2,1-d]-2-oxazolines and evaluation of their glycosylation reactivity. Carbohydr Res. 2012;356:172-9.
Pertel, S. S., Kononov, L. O., Zinin, A. I., Chirva, V. J., & Kakayan, E. S. (2012). Synthesis of some 2-alkoxy glyco-[2,1-d]-2-oxazolines and evaluation of their glycosylation reactivity. Carbohydrate Research, 356, 172-9. https://doi.org/10.1016/j.carres.2012.03.026
Pertel SS, et al. Synthesis of some 2-alkoxy Glyco-[2,1-d]-2-oxazolines and Evaluation of Their Glycosylation Reactivity. Carbohydr Res. 2012 Jul 15;356:172-9. PubMed PMID: 22521206.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of some 2-alkoxy glyco-[2,1-d]-2-oxazolines and evaluation of their glycosylation reactivity. AU - Pertel,Sergey S, AU - Kononov,Leonid O, AU - Zinin,Alexander I, AU - Chirva,Vasily Ja, AU - Kakayan,Elena S, Y1 - 2012/04/02/ PY - 2012/01/31/received PY - 2012/03/21/revised PY - 2012/03/23/accepted PY - 2012/4/24/entrez PY - 2012/4/24/pubmed PY - 2012/11/14/medline SP - 172 EP - 9 JF - Carbohydrate research JO - Carbohydr. Res. VL - 356 N2 - 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. SN - 1873-426X UR - https://www.unboundmedicine.com/medline/citation/22521206/Synthesis_of_some_2_alkoxy_glyco_[21_d]_2_oxazolines_and_evaluation_of_their_glycosylation_reactivity_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0008-6215(12)00134-6 DB - PRIME DP - Unbound Medicine ER -