Development of stereoselective glycosylation using alkoxymethyl groups and application to the total synthesis of natural products
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- Torikai Kohei
- Principal Investigator
- 九州大学
About This Project
- Japan Grant Number
- JP18K05462 (JGN)
- Funding Program
- Grants-in-Aid for Scientific Research
- Funding Organization
- Japan Society for the Promotion of Science
Kakenhi Information
- Project/Area Number
- 18K05462
- Research Category
- Grant-in-Aid for Scientific Research (C)
- Allocation Type
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- Multi-year Fund
- Review Section / Research Field
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- Basic Section 38040:Bioorganic chemistry-related
- Research Institution
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- Kyushu University
- Project Period (FY)
- 2018-04-01 〜 2023-03-31
- Project Status
- Completed
- Budget Amount*help
- 4,420,000 Yen (Direct Cost: 3,400,000 Yen Indirect Cost: 1,020,000 Yen)
Research Abstract
Before starting this project, only one example for the glycosylation of 2-O-alkoxymethyl (AM) donor, in which 1,2-cis selectivity had been observed for a 2-O-methoxymethyl donor, was reported. Contrary to it, we envisaged that reversed selectivity should appear if the oxygen atom of AM participates the oxocarbenium ion. After our considerable experimentation (with more than dozens of examples), we found that all the reactions gave 1,2-trans glycosides. Furthermore, we found that AM donors had higher reactivity than traditional 2-O-acyl donors and thus developed a one-pot iterative glycosylation strategy. In addition, during the development of the above one-pot strategy, we created a simple apparatus to add solid materials under inert atmosphere without any contamination by air.
Keywords
Details 詳細情報について
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- CRID
- 1040282256975869056
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- Text Lang
- ja
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- Data Source
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- KAKEN
