2016 Fiscal Year Final Research Report
Promotion of efficiency of glycosylation reaction based on increasing flexibility of conformation
| Project/Area Number |
15K13650
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| Research Category |
Grant-in-Aid for Challenging Exploratory Research
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| Allocation Type | Multi-year Fund |
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| Research Field |
Organic chemistry
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| Research Institution | Kwansei Gakuin University |
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Principal Investigator |
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| Research Collaborator |
IKEUCHI Kazutada
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| Project Period (FY) |
2015-04-01 – 2017-03-31
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| Keywords | 合成化学 / 糖 / 立体配座 / グリコシル化反応 |
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| Outline of Final Research Achievements |
In order to increase the efficiency of the glycosylation reaction by flexibilizing the conformation of the pyranose ring, we investigated flexibility and reactivity of glucose derivatives equipped with bridging groups between the 3- and 6-oxygens. As a result, we revealed that the use of bibenzyl-bismethylene group as the bridging group increased flexibility of the conformation of glucopyranose ring and that reactivity of the bridged glycosyl donor improved comparing to that without the bridge. In addition, we developed a highly alfa-selective glycosylation reaction using the bridged glycosyl donor. Previously, the conformation of the glycosyl donors used in the chemical glycosylation reactions have been locked; therefore, our approach is an innovative trial. Further, utilizing the alfa-selective glycosylation, we expanded our work to the synthesis of several cyclic 1,4-oligo glucosides.
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| Free Research Field |
有機合成化学
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