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 |
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Pages (from-to) | 1608-1613 |
Number of pages | 6 |
Journal | Synlett |
Volume | 28 |
Issue number | 13 |
DOIs | |
Publication status | Published - 14 Aug 2017 |
Keywords
- 4-(3-chloropropoxy)phenyl glycosides
- conformation
- glycosylation
- protecting groups
- stereoselective synthesis
- stereoselectivity
- triisopropylsilyl group
ASJC Scopus subject areas
- Organic Chemistry