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

Koov Leonid O. | Zendy; Malysheva Nelly N. | Zendy; Orlova Anna V. | Zendy

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

Author(s) -

Koov Leonid O.,

Malysheva Nelly N.,

Orlova Anna V.

Publication year - 2009

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200801017

Subject(s) - stereoselectivity , chemistry , glycosylation , glycosyl , anomer , stereochemistry , supramolecular chemistry , combinatorial chemistry , organic chemistry , catalysis , molecule , biochemistry

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)

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