α-Selective Glycosylation with β-Glycosyl Sulfonium Ions Prepared via Intramolecular Alkylation | Zendy

Sam J. Moons | Zendy; Rens A. Mensink | Zendy; Jeroen P.J. Bruekers | Zendy; Maurits L. A. Vercammen | Zendy; Laura M. Jansen | Zendy; Thomas J. Boltje | Zendy

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α-Selective Glycosylation with β-Glycosyl Sulfonium Ions Prepared via Intramolecular Alkylation

Author(s) -

Sam J. Moons,

Rens A. Mensink,

Jeroen P.J. Bruekers,

Maurits L. A. Vercammen,

Laura M. Jansen,

Thomas J. Boltje

Publication year - 2019

Publication title -

the journal of organic chemistry

Language(s) - Uncategorized

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b00022

Subject(s) - sulfonium , chemistry , intramolecular force , glycosyl , stereoselectivity , glycosylation , substituent , alkylation , anomer , stereochemistry , glycosyl donor , combinatorial chemistry , organic chemistry , catalysis , salt (chemistry) , biochemistry

Stereoselective glycosylation remains the main challenge in the chemical synthesis of oligosaccharides. Herein we report a simple method to convert thioglycosides into β-sulfonium ions via an intramolecular alkylation reaction, leading to highly α-selective glycosylations for a variety of glycosyl acceptors. The influence of the thioglycoside substituent and the protecting group pattern on the glycosyl donor was investigated and showed a clear correlation with the observed stereoselectivity.

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