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 output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)1608-1613
Number of pages6
JournalSynlett
Volume28
Issue number13
DOIs
Publication statusPublished - 14 Aug 2017

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Thiogalactosides
Monosaccharides
Disaccharides
Oligosaccharides
Cations

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 journalArticle

Abronina, Polina I. ; Zinin, Alexander I. ; Malysheva, Nelly N. ; Stepanova, Elena V. ; Chizhov, Alexander O. ; Torgov, Vladimir I. ; Kononov, Leonid O. / A Novel Glycosyl Donor with a Triisopropylsilyl Nonparticipating Group in Benzyl-Free Stereoselective 1,2- cis -Galactosylation. In: Synlett. 2017 ; Vol. 28, No. 13. pp. 1608-1613.
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AU - Malysheva, Nelly N.

AU - Stepanova, Elena V.

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AU - Torgov, Vladimir I.

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