2016 Fiscal Year Final Research Report
Study on the development of novel glycosylation reaction using hypervalent iodine
| Project/Area Number |
26460022
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Multi-year Fund |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | Ritsumeikan University |
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Principal Investigator |
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Keywords | グリコシル化 / 超原子価ヨウ素 / チオグリコシド / 無臭ベンゼンチオール |
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| Outline of Final Research Achievements |
Ｔhioglycosides were first prepared as the glycosyl donors by using odorless p-octyloxybenzenethiol and peracetates of monosaccharides in the presence of BF3 Et2O. And then, the thioglycosides were activated with diverse hypervalent iodines in the presence of some protic or Lewis acids to investigate the best condition to obtain desired glycosides. Finally, we could found that reactions with phenyliodine bis(trifluoroacetate) (1 eq.) in the presence of trifluoromethanesulfonic acid (2 eq.) afforded satisfactory results. Especially, when thioglycosides of N-phthaloyl-3,4,6-tri-O-acetyl-D-glucosamine or N-phthaloyl-3,4,6-tri-O-acetylD-galactosamine were employed as the glycosyl donors, the reactions proceeded in excellent chemical yields with high beta-selectivities. By using the present method, we could succeeded in the preparation of terpene glycoside as well as disaccharide derivatives even in the case that the acceptor alcohols were sterically hindered.
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| Free Research Field |
有機化学
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