A Study on Glycosylation Reaction in Fluorous Biphasic System
| Project/Area Number |
17350052
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| Research Category |
Grant-in-Aid for Scientific Research (B)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Tokai University |
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Principal Investigator |
INAZU Toshiyuki Tokai University, School of Engineering, Professor (70151579)
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| Project Period (FY) |
2005 – 2007
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| Project Status |
Completed (Fiscal Year 2007)
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| Budget Amount *help |
¥10,410,000 (Direct Cost: ¥9,600,000、Indirect Cost: ¥810,000)
Fiscal Year 2007: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2006: ¥3,900,000 (Direct Cost: ¥3,900,000)
Fiscal Year 2005: ¥3,000,000 (Direct Cost: ¥3,000,000)
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| Keywords | Fluorous Synthesis / Oligosaccharide Synthesis / Oligosaccharide Synthesizer / Biphasic System / Glycosylation Reaction / Micro Reactor / 二層系反応 / フルオラス糖鎖合成 / フルオラスイミデート法 / 液滴 / フルオラスタグ / クラウンエーテル |
|---|
| Research Abstract |
1) First we tried the glycosylation reaction using glycosyl donors having fluorous leaving groups. Although the derivatives of mannosyl fluoride and mannosyl Nphenyltrifluoroacetimidate gave the corresponding glycosides in good yields under homogeneous conditions [Et2O-NovecTM(2:1)], no glycoside was observed by TLC under fluorous biphasic system [organic solvent-FluorinertTM FC-72].
2) Next, we designed and synthesized the derivative of mannosyl Nphenylpentadecafluorooctanoimidate as a new fluorous glycosyl donor. This new donor gave the glycoside in high yield only under homogeneous conditions similar to that of N-phenyltrifluoroacetimidate.
3) Finally, we found the 6- O-Hfb (fluorous protecting group) derivative of mannosyl trichloroacetimidate without a fluorous leaving group gave the corresponding glycoside in good yield under fluorous biphasic conditions [dichloromethane-FC-72].
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Report
(4 results)
Research Products
(38 results)
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[Journal Article] Monovalent Gb3-/Gb2-Derivatives Conjugated with a Phosphatidyl Residue : A Novel Class of Shiga Toxin-Neutralizing Agent2007
Author(s)
P., Neri, S., Tokoro, S., -I., Yokoyama, T., Miura, T., Murata, Y., Nishida, T., Kajimoto, S., Tsujino, T., Inazu, T., Usui, H., Mori
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Journal Title
Biol. Pharm. Bull 30(9)
Pages: 1697-1701
Description
「研究成果報告書概要(欧文)」より
Related Report
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[Journal Article] Fluorescence Modification of Gb3 Oligosaccharide and Rapid Synthesis of Oligosaccharide Moieties Using Fluorous Protective Group2005
Author(s)
T., Miura, S., Tsujino, A., Satoh, K., Goto, M., Mizuno, M., Noguchi, T., Kajimoto, M., Node, Y., Murakami, N., Imai, T., Inazu
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Journal Title
Tetrahedron 61
Pages: 6518-6526
Description
「研究成果報告書概要(欧文)」より
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[Journal Article] A Novel Benzoyl-type Fluorous Protecting Group for Use in Fluorous Synthesis2005
Author(s)
T., Miura, A., Satoh, K., Goto, Y., Murakami, N., Imai, T., Inazu
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Journal Title
Tetrahedron Assym 16(1)
Pages: 3-6
Description
「研究成果報告書概要(欧文)」より
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