A Novel Glycosyl Donor with a Triisopropylsilyl Nonparticipating Group in Benzyl-Free Stereoselective 1,2- cis -Galactosylation

Polina I. Abronina, Alexander I. Zinin, Nelly N. Malysheva, Elena V. Stepanova, Alexander O. Chizhov, Vladimir I. Torgov, Leonid O. Kononov

Research School of Chemistry & Applied Biomedical Sciences

Research output: Contribution to journal › Article

6 Citations (Scopus)

Abstract

A novel glycosyl donor with a triisopropylsilyl (TIPS) nonparticipating group at O-2 is introduced for use in 1,2- cis -galactosylation. Coupling the 2- O -TIPS-substituted thiogalactoside donor with a series of mono- and disaccharide glycosyl acceptors was found to lead exclusively to α-linked oligosaccharides. The observed exceptionally high α-selectivity was interpreted in terms of conformational changes in the glycosyl cation induced by the bulky 2- O -TIPS group.

Original language	English
Pages (from-to)	1608-1613
Number of pages	6
Journal	Synlett
Volume	28
Issue number	13
DOIs	https://doi.org/10.1055/s-0036-1589028
Publication status	Published - 14 Aug 2017

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Keywords

4-(3-chloropropoxy)phenyl glycosides
conformation
glycosylation
protecting groups
stereoselective synthesis
stereoselectivity
triisopropylsilyl group

ASJC Scopus subject areas

Organic Chemistry

Cite this

Abronina, P. I., Zinin, A. I., Malysheva, N. N., Stepanova, E. V., Chizhov, A. O., Torgov, V. I., & Kononov, L. O. (2017). A Novel Glycosyl Donor with a Triisopropylsilyl Nonparticipating Group in Benzyl-Free Stereoselective 1,2- cis -Galactosylation. Synlett, 28(13), 1608-1613. https://doi.org/10.1055/s-0036-1589028

A Novel Glycosyl Donor with a Triisopropylsilyl Nonparticipating Group in Benzyl-Free Stereoselective 1,2- cis -Galactosylation. / Abronina, Polina I.; Zinin, Alexander I.; Malysheva, Nelly N.; Stepanova, Elena V.; Chizhov, Alexander O.; Torgov, Vladimir I.; Kononov, Leonid O.

In: Synlett, Vol. 28, No. 13, 14.08.2017, p. 1608-1613.

Research output: Contribution to journal › Article

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AU - Zinin, Alexander I.

AU - Malysheva, Nelly N.

AU - Stepanova, Elena V.

AU - Chizhov, Alexander O.

AU - Torgov, Vladimir I.

AU - Kononov, Leonid O.

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Access to Document

10.1055/s-0036-1589028