Synthesis of chiral auxiliary and multi-activation ligand having phosphonylated sugar moiety and their application for asymmetric synthesis
| Project/Area Number |
14550823
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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 |
Synthetic chemistry
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| Research Institution | Shinshu University |
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Principal Investigator |
IWAO Yamamoto Shinshu University, Department of Functional Polymer Science, Professor, 繊維学部, 教授 (60021169)
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| Co-Investigator(Kenkyū-buntansha) |
FUJIMOTO Tetsuya Shinshu University, Department of Functional Polymer Science, Associate Professor, 繊維学部, 助教授 (90209099)
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| Project Period (FY) |
2002 – 2003
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| Project Status |
Completed (Fiscal Year 2003)
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| Budget Amount *help |
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2003: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 2002: ¥2,300,000 (Direct Cost: ¥2,300,000)
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| Keywords | chiral auxiliary / Diels-Alder reaction / phosphonylated sugar / asymmetric synthesis / phosphenium cation / 不斉補助基 / ジアステレオ選択的 |
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| Research Abstract |
Reaction of methyl 4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranoside with two equivalents of diphenylphosphenium cation at 0° C gave the α-and β-1-phosphonylated 2-enopyranosides as major products. Similarly, Reaction of diphenylphosphenium cation with tri-O-acetylglycal afforded the same products in a similar ratio. By contrast, a reaction with tri-O-benzylglucal at reflux temperature of dichloromethane afforded the 3-phosphonylated sugar as a major product. These reactions would proceed via stable allyl cations. Furthermore, the 3-phosphonylated sugar was useful for chiral auxiliary. For example, Diels-Alder reaction of an acrylate ester of the 3-phosphonylated sugar with eyclopentadiene gave a cycloadduct in good yield with excellent diastereoselectiviry.
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Report
(3 results)
Research Products
(3 results)
