2022 Fiscal Year Final Research Report
Diastereoselective Desymmetric 1,2-cis-Glycosylation and Its Application to the Synthesis of Useful Glycosides
| Project/Area Number |
19H02724
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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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| Review Section |
Basic Section 33020:Synthetic organic chemistry-related
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| Research Institution | Keio University |
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Principal Investigator |
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| Project Period (FY) |
2019-04-01 – 2023-03-31
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| Keywords | 非対称化 / グリコシル化反応 / 有用糖質合成 / 立体選択性 / 位置選択性 / ホウ素触媒 / メソジオール / 1,2-シスグリコシド |
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| Outline of Final Research Achievements |
The aim of this study was to develop a novel and highly diastereoselective desymmetric 1,2-cis-stereoselective glycosylation of meso-diols using a boronic acid catalyst based on predictions of regioselectivity and to apply the reaction to the synthesis of useful carbohydrates. As a result, we succeeded in developing a highly diastereoselective desymmetric 1,2-cis-stereoselective glycosylation of a myo-inositol derivative and a 1,2-anhydrosugar using a boronic acid catalyst. It was also demonstrated that this method is applicable to acyclic meso-diols. Furthermore, the synthesis of some core structures of useful carbohydrates including LL-BM782s using this reaction was achieved. Moreover, a synthetic study toward the total synthesis of the antibiotic kanamycin A was conducted, which provided a good guideline for the future.
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| Free Research Field |
有機合成化学、糖質化学、ケミカルバイオロジー
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| Academic Significance and Societal Importance of the Research Achievements |
本研究で開発したメソジオールの非対称化型1,2-cis-立体選択的グリコシル化反応を利用することで、生成し得る４つのジアステレオマーの中から、望みの１つの配糖体を効率的に合成可能となった。すなわち、従来のキラル保護基の保護・脱保護工程を経ることなく、メソジオールに対して最高100%の転換率でキラルな配糖体を1工程で供給可能となり、工程数の削減と収率の大幅な向上に成功した。そのため本手法は、有用糖質合成への応用が期待でき、糖質が関与する生命現象の解明や糖鎖医薬の創製に大きく貢献すると期待される、以上の点から、本研究の成果は、今後の学術面のみならず社会における貢献度も大きいと言える。
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