Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors
The glycosylation of O-glycosyl trichloroacetimidate donors using a synergistic catalytic system of electron-deficient pyridinium salts/aryl thiourea derivatives at room temperature is demonstrated. The acidity of the adduct formed by the 1,2-addition of alcohol to the electron-deficient pyridinium...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2017-11-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.13.236 |
| _version_ | 1818732735229853696 |
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| author | Mukta Shaw Yogesh Kumar Rima Thakur Amit Kumar |
| author_facet | Mukta Shaw Yogesh Kumar Rima Thakur Amit Kumar |
| author_sort | Mukta Shaw |
| collection | DOAJ |
| description | The glycosylation of O-glycosyl trichloroacetimidate donors using a synergistic catalytic system of electron-deficient pyridinium salts/aryl thiourea derivatives at room temperature is demonstrated. The acidity of the adduct formed by the 1,2-addition of alcohol to the electron-deficient pyridinium salt is increased in the presence of an aryl thiourea derivative as an hydrogen-bonding cocatalyst. This transformation occurs under mild reaction conditions with a wide range of O-glycosyl trichloroacetimidate donors and glycosyl acceptors to afford the corresponding O-glycosides in moderate to good yields with predictable selectivity. In addition, the optimized method is also utilized for the regioselective O-glycosylation by using a partially protected acceptor. |
| first_indexed | 2024-12-17T23:38:17Z |
| format | Article |
| id | doaj.art-690dd0231b6a4dfeb2e4d42525c02f95 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T23:38:17Z |
| publishDate | 2017-11-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-690dd0231b6a4dfeb2e4d42525c02f952022-12-21T21:28:30ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-11-011312385239510.3762/bjoc.13.2361860-5397-13-236Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donorsMukta Shaw0Yogesh Kumar1Rima Thakur2Amit Kumar3Department of Chemistry, Indian Institute of Technology Patna, Bihta 801106, Bihar, IndiaDepartment of Chemistry, Indian Institute of Technology Patna, Bihta 801106, Bihar, IndiaDepartment of Chemistry, National Institute of Technology Patna, Patna 800005, Bihar, IndiaDepartment of Chemistry, Indian Institute of Technology Patna, Bihta 801106, Bihar, IndiaThe glycosylation of O-glycosyl trichloroacetimidate donors using a synergistic catalytic system of electron-deficient pyridinium salts/aryl thiourea derivatives at room temperature is demonstrated. The acidity of the adduct formed by the 1,2-addition of alcohol to the electron-deficient pyridinium salt is increased in the presence of an aryl thiourea derivative as an hydrogen-bonding cocatalyst. This transformation occurs under mild reaction conditions with a wide range of O-glycosyl trichloroacetimidate donors and glycosyl acceptors to afford the corresponding O-glycosides in moderate to good yields with predictable selectivity. In addition, the optimized method is also utilized for the regioselective O-glycosylation by using a partially protected acceptor.https://doi.org/10.3762/bjoc.13.236cooperative catalysiselectron-deficient pyridinium saltsO-glycosideregioselectivitythiourea |
| spellingShingle | Mukta Shaw Yogesh Kumar Rima Thakur Amit Kumar Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors Beilstein Journal of Organic Chemistry cooperative catalysis electron-deficient pyridinium salts O-glycoside regioselectivity thiourea |
| title | Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors |
| title_full | Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors |
| title_fullStr | Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors |
| title_full_unstemmed | Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors |
| title_short | Electron-deficient pyridinium salts/thiourea cooperative catalyzed O-glycosylation via activation of O-glycosyl trichloroacetimidate donors |
| title_sort | electron deficient pyridinium salts thiourea cooperative catalyzed o glycosylation via activation of o glycosyl trichloroacetimidate donors |
| topic | cooperative catalysis electron-deficient pyridinium salts O-glycoside regioselectivity thiourea |
| url | https://doi.org/10.3762/bjoc.13.236 |
| work_keys_str_mv | AT muktashaw electrondeficientpyridiniumsaltsthioureacooperativecatalyzedoglycosylationviaactivationofoglycosyltrichloroacetimidatedonors AT yogeshkumar electrondeficientpyridiniumsaltsthioureacooperativecatalyzedoglycosylationviaactivationofoglycosyltrichloroacetimidatedonors AT rimathakur electrondeficientpyridiniumsaltsthioureacooperativecatalyzedoglycosylationviaactivationofoglycosyltrichloroacetimidatedonors AT amitkumar electrondeficientpyridiniumsaltsthioureacooperativecatalyzedoglycosylationviaactivationofoglycosyltrichloroacetimidatedonors |