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

Результат исследований: Материалы для журналаСтатья

8 Цитирования (Scopus)

Аннотация

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.

Язык оригиналаАнглийский
Страницы (с-по)1608-1613
Число страниц6
ЖурналSynlett
Том28
Номер выпуска13
DOI
СостояниеОпубликовано - 14 авг 2017

ASJC Scopus subject areas

  • Organic Chemistry

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  • Цитировать

    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