Stereoselectivity of Glycosylation May Change During the Reaction Course: Highly α‐Stereoselective Sialylation Achieved by Supramer Approach

Stereoselectivity of Glycosylation May Change During the Reaction Course: Highly α‐Stereoselective Sialylation Achieved by Supramer Approach Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2009, Volume: 2009, Number: 5, Pages: 611-616 Pages count : 6 DOI: 10.1002/ejoc.200801017

Authors

Kononov Leonid O. ¹ , Malysheva Nelly N. ¹ , Orlova Anna V. ¹

Affiliations

1	N. K. Kochetkov Laboratory of Carbohydrate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, 119991 Moscow, Russian Federation, Fax: +7-499-137-6148

The stereoselectivity of NIS/TfOH-promoted glycosylation with O-acetylated N-acetylneuraminic acid phenyl thioglycoside was found to be dependent on the reaction time. Highly α-stereoselective sialylation (27:1 anomer ratio) was achieved by decreasing the reaction time (from 3 h to 15 min) and by adding a non-reacting compound (1 equiv.) capable of modifying the structure of hydrogen-bonded supramolecular aggregates (supramers) of the glycosyl donor. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

Kononov L.O. , Malysheva N.N. , Orlova A.V.
Stereoselectivity of Glycosylation May Change During the Reaction Course: Highly α‐Stereoselective Sialylation Achieved by Supramer Approach
European Journal of Organic Chemistry. 2009. V.2009. N5. P.611-616. DOI: 10.1002/ejoc.200801017 WOS Scopus OpenAlex

Web of science:	WOS:000263512300002
Scopus:	2-s2.0-60849132727
OpenAlex:	W2157608443

DB	Citing
OpenAlex	48
Scopus	48
Web of science	50