1997 Fiscal Year Final Research Report Summary
Study for New Lewic acid. Prepared from Bf_8・OEt_2 and Trialkylsilyl derwatives.
| Project/Area Number |
08672439
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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 | HEALTH SCIENCES UNIVERSITY OF HOKKAIDO |
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Principal Investigator |
HORITA Kiyoshi Health Sciences University of Hokkaido, Faculty of Pharmaceutical Sciences, Associate Professor., 薬学部, 助教授 (50181540)
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| Project Period (FY) |
1996 – 1997
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| Keywords | Boron trifluoride etherate / Trimethylsilyl triflate / New Lewis Acid / acetonitrile / Metal exchange reaction / C-Glycosidation |
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| Research Abstract |
1.Boron trifluoride diethyl etherate (BF_3・Oet_2) and trimethylsilyl triflate are the most representative Lewis acids in many kinds of Lewis acids. We found that these two Lewis acids easily and quickly reacted in acetonitrile to give a new Lewis acid (BF_2(OTf)). This new chemical species was identified by ^1H,^<11>B,^<19>FNMR experiments. When 1 equivalent of boron trifluoride etherate was combinated with 1 equivalent of trimethylsilyl triflate in 1 : 1 ratio in CD_3CN,a methyl signal of CH_3OTf at 0.5 ppm (broad singlet) disappered and one set of doublet (J=7.5 Hz) at 0.2 ppm was observed as a methyl signal of trimethylsilyl fluoride in ^1HNMR.Furthermore, decatet signal (J=7.5 Hz) was observed in ^<19>FNMR based on a trimethylsilyl fluoride. It was found that trialkylsilyl derivatives such as trimethylsilyl methanesulfonate, trimethylsilylmethyl ether, triethylsilane and trimethylallylsilane generally reacted with boron trifluoride in acetonitrile.
2.It was found that C-allylglycosidation reaction of methylidopyranosyl derivative with free hydroxy groups proceeded efficiently and stereoselectively when this newly develoved BF_2OTf was used.
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