Synthetic carbohydrate research based on organic electrochemistry
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....
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| Veröffentlicht in: | Carbohydrate research 2012-12, Vol.363, p.1-6 |
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| container_title | Carbohydrate research |
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| creator | Nokami, Toshiki Saito, Kodai Yoshida, Jun-ichi |
| description | 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. |
| doi_str_mv | 10.1016/j.carres.2012.09.023 |
| format | Article |
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| ispartof | Carbohydrate research, 2012-12, Vol.363, p.1-6 |
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| language | eng |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Anodic oxidation Carbohydrates - chemical synthesis Carbohydrates - chemistry cations Chemistry Techniques, Synthetic - instrumentation Chemistry Techniques, Synthetic - methods electrochemistry Electrochemistry - instrumentation Electrochemistry - methods Electrolytes - chemistry Glycosyl triflate Glycosylation methodology Oligosaccharide oligosaccharides Oligosaccharides - chemical synthesis Oligosaccharides - chemistry oxidation |
| title | Synthetic carbohydrate research based on organic electrochemistry |
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