Regio-and stereoselective phosphonylation of sugars and its application for anti-cancer and anti-HIV agen
| Project/Area Number |
07555588
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| Research Category |
Grant-in-Aid for Scientific Research (A)
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| Allocation Type | Single-year Grants |
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| Section | 展開研究 |
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| Research Field |
Synthetic chemistry
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| Research Institution | Shinshu University |
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Principal Investigator |
YAMAMOTO Iwao Shinshu University, Dept.Textile Science & Technology, Professor, 繊維学部, 教授 (60021169)
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| Co-Investigator(Kenkyū-buntansha) |
KASAKA Tatsuji Terra Chem Inc., Vice President, 副社長
FUJIMOTO Tetsuya Shinshu University, Dept.Textile Science & Technology, Assistant Professor, 繊維学部, 助手 (90209099)
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| Project Period (FY) |
1995 – 1997
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| Project Status |
Completed (Fiscal Year 1997)
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| Budget Amount *help |
¥4,100,000 (Direct Cost: ¥4,100,000)
Fiscal Year 1997: ¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 1996: ¥2,200,000 (Direct Cost: ¥2,200,000)
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| Keywords | phosphenium cation / unsaturated sugar / bioactive / ホスフェニウムイオン / ホスホン化糖 / 抗HIV剤 / 抗腫瘍剤 |
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| Research Abstract |
Reaction of tri-O-acetylglucal with chloro (diisopropylamino) phosphenium cation gave 1-phosphonylated 2-eno-pyranoside stereo and regioselectivily. After deprotection, endothelin receptor binding accey of the deprotected phosphonylated sugar was investigated, but good results were not obtained.
On the other hand, reaction of tri-O-acetylgulucal with diphenylphosphenium cation in dichloromethane, unsaturated sugars having phosphinoyl group on 1-and 3-position was obtained in 51% (1-alpha), 21% (1-beta), and 6% (3-peudaxial), respectively. The stereochemistry of these products were determined by their NOESY spectra. The ozonolysis of 1-phospinoyl-unsaturated sugar in dichloromethane at -78ﾟC gave dialdehyde which cyclyzed in intramolecular aldol-type reaction manner gave franoside in 41% yield. These results will be published elsewhere.
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Report
(4 results)
Research Products
(2 results)
