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

descriptionPublicationkeyboard_double_arrow_right Article 08 May 2017 Russian Federation English Publisher:Georg Thieme Verlag KGJournal:Synlett, volume 28, pages 1,608-1,613 (issn: 0936-5214, eissn: 1437-2096,

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Authors: Leonid Kononov; Polina Abronina; Alexander Zinin; Nelly Malysheva; Elena Stepanova; Alexander Chizhov; Vladimir Torgov;

doi: 10.1055/s-0036-1589028

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

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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.

Country

Russian Federation

Related Organizations

Tomsk Polytechnic University
Russian Federation
Russian Academy of Sciences
Russian Federation
N.D. Zelinsky Institute of Organic Chemistry
Russian Federation

Keywords

conformation, стереоселективный синтез, стереоселективность, glycosylation, triisopropylsilyl group, 4-(3-chloropropoxy)phenyl glycosides, защитные группы, конформация, stereoselectivity, фенилгликозиды, гликозилирование, protecting groups, stereoselective synthesis

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