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

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

Journal

Synlett
ISSN: 0936-5214 , E-ISSN: 1437-2096

Output data

Year: 2017, Volume: 28, Number: 13, Pages: 1608-1613 Pages count : 6 DOI: 10.1055/s-0036-1589028

Authors

Abronina Polina I. ¹ , Zinin Alexander I. ¹ , Malysheva Nelly N. ¹ , Stepanova Elena V. ¹ , Chizhov Alexander O. ^2,1 , Torgov Vladimir I. ¹ , Kononov Leonid O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
2	Department of Biotechnology and Organic Chemistry, National Research Tomsk Polytechnic University

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.

Abronina P.I. , Zinin A.I. , Malysheva N.N. , Stepanova E.V. , Chizhov A.O. , Torgov V.I. , Kononov L.O.
A Novel Glycosyl Donor with a Triisopropylsilyl Nonparticipating Group in Benzyl-Free Stereoselective 1,2-cis-Galactosylation
Synlett. 2017. V.28. N13. P.1608-1613. DOI: 10.1055/s-0036-1589028 WOS Scopus OpenAlex

Web of science:	WOS:000408092200022
Scopus:	2-s2.0-85019158185
OpenAlex:	W2613633463

DB	Citing
OpenAlex	31
Scopus	30
Web of science	30