Glycosyl Sulfonium Ions as Storable Intermediates for Glycosylations

Glycosyl sulfonium ions, which serve as persistent glycosyl cation equivalents, were prepared by the addition of diorganosulfides to an electrochemically generated glycosyl triflate. Low-temperature and variable-temperature NMR studies were performed to reveal the structure, stability, and reactivit...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2011-03, Vol.13 (6), p.1544-1547
Main Authors: Nokami, Toshiki, Nozaki, Yuki, Saigusa, Yoshihiro, Shibuya, Akito, Manabe, Shino, Ito, Yukishige, Yoshida, Jun-ichi
Format: Article
Language:English
Subjects:
Combinatorial Chemistry Techniques
Glycosides - chemical synthesis
Glycosides - chemistry
Glycosylation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Sulfonium Compounds - chemical synthesis
Sulfonium Compounds - chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Glycosyl sulfonium ions, which serve as persistent glycosyl cation equivalents, were prepared by the addition of diorganosulfides to an electrochemically generated glycosyl triflate. Low-temperature and variable-temperature NMR studies were performed to reveal the structure, stability, and reactivity of glycosyl sulfonium ions. The glycosyl sulfonium ions could be used as storable intermediates for reactions with various glycosyl acceptors including thioglycosides to give the corresponding disaccharides.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200242u