| Project/Area Number |
13672227
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Chemical pharmacy
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| Research Institution | FACULTY OF PHARMACEUTICAL SCIENCES HEALTH SCIENCES UNIVERSITY OF HOKKAIDO |
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Principal Investigator |
HORITA Kiyoshi FACULTY OF PHARMACEUTICAL SCIENCES HEALTH SCIENCES UNIVERSITY OF HOKKAIDO, ASSOCIATE PROFESSOR, 薬学部, 助教授 (50181540)
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| Project Period (FY) |
2001 – 2002
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| Project Status |
Completed (Fiscal Year 2002)
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| Budget Amount *help |
¥3,400,000 (Direct Cost: ¥3,400,000)
Fiscal Year 2002: ¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 2001: ¥1,800,000 (Direct Cost: ¥1,800,000)
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| Keywords | BF_3-Oet_2 / Me_3SiOTf / Lewis acid / C-allylglycosidation / BF_2(Otf) / ルイス酸 / トリメチルシリルトソフラート / 三フッ化ホウ素エーテル錯体 / C-アリルグリコシル化 / アリル-C-グリコシル化 |
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| Research Abstract |
We found a new Lewis acid which were easily generated from BF_3-Oet_2 complex and Me_3SiOTf in 1:1 ratio, as the most general and popular Lewis acid in organic synthesis, in acetonitrile. Structure of the newly generated Lewis acid were determined as BF_2(Otf) by measurement of ^1H-NMR, ^<19>F-NMR abd ^<11>B-NMR. The most important information from those NMR measurement results was detection of the Me_3SiF. Generation of the molecular spices indicates that transmetalation reaction take place quickly between BF_3-Oet_2 complex and Me_3SiOTf in acetonitrile.
This newly developed Lewis acid, as BF_2(Otf), was examined toward some Lewis acid mediated organic reactions. It found that this new Lewis acid was very useful. Especially, highly stereocontrolled C-allylglycosidation reaction efficiently took place toward some kinds of methyl pyranose derivatives, idose, glucose and galactose, with free hydroxyl groups (no protecting groups)
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