Abstract
Development of a novel method for generating glycosyl cations or their equivalents is highly desired, because such intermediates are crucial for developing stereoselective glycosylations in oligosaccharide syntheses. In this review we focus on electrochemical methods that we have recently developed. The anodic oxidation of thioglycosides is effective for generating glycosyl triflate pools, which react with glycosyl acceptors. The reaction of glycosyl triflate pools with diorganosulfides gives glycosyl sulfonium ions, which also serve as effective glycosylation intermediates. The indirect electrochemical method is effective for the generation of glycosyl cations or their equivalents and the use of a flow-microreactor system enables glycosylation using such intermediates.
| Original language | English |
|---|---|
| Pages (from-to) | 1-6 |
| Number of pages | 6 |
| Journal | Carbohydrate Research |
| Volume | 363 |
| DOIs | |
| Publication status | Published - 2012 Dec 1 |
| Externally published | Yes |
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Keywords
- Anodic oxidation
- Glycosyl triflate
- Glycosylation
- Oligosaccharide
ASJC Scopus subject areas
- Biochemistry
- Analytical Chemistry
- Organic Chemistry
Cite this
Synthetic carbohydrate research based on organic electrochemistry. / Nokami, Toshiki; Saito, Kodai; Yoshida, Jun Ichi.
In: Carbohydrate Research, Vol. 363, 01.12.2012, p. 1-6.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthetic carbohydrate research based on organic electrochemistry
AU - Nokami, Toshiki
AU - Saito, Kodai
AU - Yoshida, Jun Ichi
PY - 2012/12/1
Y1 - 2012/12/1
N2 - Development of a novel method for generating glycosyl cations or their equivalents is highly desired, because such intermediates are crucial for developing stereoselective glycosylations in oligosaccharide syntheses. In this review we focus on electrochemical methods that we have recently developed. The anodic oxidation of thioglycosides is effective for generating glycosyl triflate pools, which react with glycosyl acceptors. The reaction of glycosyl triflate pools with diorganosulfides gives glycosyl sulfonium ions, which also serve as effective glycosylation intermediates. The indirect electrochemical method is effective for the generation of glycosyl cations or their equivalents and the use of a flow-microreactor system enables glycosylation using such intermediates.
AB - Development of a novel method for generating glycosyl cations or their equivalents is highly desired, because such intermediates are crucial for developing stereoselective glycosylations in oligosaccharide syntheses. In this review we focus on electrochemical methods that we have recently developed. The anodic oxidation of thioglycosides is effective for generating glycosyl triflate pools, which react with glycosyl acceptors. The reaction of glycosyl triflate pools with diorganosulfides gives glycosyl sulfonium ions, which also serve as effective glycosylation intermediates. The indirect electrochemical method is effective for the generation of glycosyl cations or their equivalents and the use of a flow-microreactor system enables glycosylation using such intermediates.
KW - Anodic oxidation
KW - Glycosyl triflate
KW - Glycosylation
KW - Oligosaccharide
UR - http://www.scopus.com/inward/record.url?scp=84867589528&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84867589528&partnerID=8YFLogxK
U2 - 10.1016/j.carres.2012.09.023
DO - 10.1016/j.carres.2012.09.023
M3 - Article
C2 - 23089173
AN - SCOPUS:84867589528
VL - 363
SP - 1
EP - 6
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
ER -