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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| Co-Investigator(Kenkyū-buntansha) |
北 泰行 立命館大学, 総合科学技術研究機構, 教授 (00028862)
森本 功治 立命館大学, 薬学部, 助教 (10543952)
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| Project Period (FY) |
2014-04-01 – 2017-03-31
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| Project Status |
Completed (Fiscal Year 2016)
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| Budget Amount *help |
¥5,070,000 (Direct Cost: ¥3,900,000、Indirect Cost: ¥1,170,000)
Fiscal Year 2016: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2015: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2014: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
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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 / 無臭チオール / 環境調和型 / PIFA / トリフルオロメタンスルホン酸 |
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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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Report
(4 results)
Research Products
(12 results)
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[Journal Article] Mechanistic Aspects of Asymmetric Intramolecular Heck Reaction Involving Dynamic Kinetic Resolution: Flexible Conformation of the Cyclohexenylidene-benzene System2015
Author(s)
S. Hosoi, M. Ozeki, M. Nakano, K. Arimitsu, T. Kajimoto, N. Kojima, H. Iwasaki, T. Miura, H. Kimura, M. Node, M. Yamashita
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Journal Title
Tetrahedron
Volume: 71
Issue: 15
Pages: 2317-2326
DOI
Related Report
Peer Reviewed / Open Access
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[Journal Article] Concise High Stereoselective Synthesis of (E)-alfa-Substituted-alfa, beta-Unsaturated Esters2015
Author(s)
M. Ozeki, S. Izumiya, D. Nakashima, H. Egawa, A. Kuse, T. Takano, H. Mizutani, N. Yasuda, K. Arimitsu, T. Kajimoto, S. Hosoi, H. Iwasaki, N. Kojima, M. Node, M. Yamashita
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Journal Title
Synthesis
Volume: 2015
Issue: 21
Pages: 3392-3402
DOI
Related Report
Peer Reviewed / Open Access
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