Palladium-catalyzed stereoselective C-glycosylation of glycals with sodium arylsulfinates
An efficient glycosylation method to synthesize 2-deoxy-C-aryl glycosides was developed. This C-glycosylation strategy is based on a palladium-catalyzed desulfitative Ferrier-type coupling reaction of glycals and sodium arylsulfinates. A series of C-aryl glycosides were obtained in moderate to good...
| Main Authors: | , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2015
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| Online Access: | https://hdl.handle.net/10356/106693 http://hdl.handle.net/10220/25083 http://dx.doi.org/10.1002/ejoc.201403550 |
| _version_ | 1811691031900454912 |
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| author | Ma, Jimei Xiang, Shaohua Jiang, Hong Liu, Xue-Wei |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Ma, Jimei Xiang, Shaohua Jiang, Hong Liu, Xue-Wei |
| author_sort | Ma, Jimei |
| collection | NTU |
| description | An efficient glycosylation method to synthesize 2-deoxy-C-aryl glycosides was developed. This C-glycosylation strategy is based on a palladium-catalyzed desulfitative Ferrier-type coupling reaction of glycals and sodium arylsulfinates. A series of C-aryl glycosides were obtained in moderate to good yields with exclusive regio- and stereoselectivities. The anomeric selectivity was found to depend on the configuration of the C3 substituent of the glycals. |
| first_indexed | 2024-10-01T06:13:26Z |
| format | Journal Article |
| id | ntu-10356/106693 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2024-10-01T06:13:26Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-10356/1066932019-12-06T22:16:25Z Palladium-catalyzed stereoselective C-glycosylation of glycals with sodium arylsulfinates Ma, Jimei Xiang, Shaohua Jiang, Hong Liu, Xue-Wei School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry An efficient glycosylation method to synthesize 2-deoxy-C-aryl glycosides was developed. This C-glycosylation strategy is based on a palladium-catalyzed desulfitative Ferrier-type coupling reaction of glycals and sodium arylsulfinates. A series of C-aryl glycosides were obtained in moderate to good yields with exclusive regio- and stereoselectivities. The anomeric selectivity was found to depend on the configuration of the C3 substituent of the glycals. 2015-02-24T07:01:40Z 2019-12-06T22:16:25Z 2015-02-24T07:01:40Z 2019-12-06T22:16:25Z 2015 2015 Journal Article Ma, J., Xiang, S., Jiang, H., & Liu, X.-W. (2015). Palladium-catalyzed stereoselective C-glycosylation of glycals with sodium arylsulfinates. European journal of organic chemistry, 2015(5), 949-952. 1434-193X https://hdl.handle.net/10356/106693 http://hdl.handle.net/10220/25083 http://dx.doi.org/10.1002/ejoc.201403550 en European journal of organic chemistry © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry::Organic chemistry Ma, Jimei Xiang, Shaohua Jiang, Hong Liu, Xue-Wei Palladium-catalyzed stereoselective C-glycosylation of glycals with sodium arylsulfinates |
| title | Palladium-catalyzed stereoselective C-glycosylation of glycals with sodium arylsulfinates |
| title_full | Palladium-catalyzed stereoselective C-glycosylation of glycals with sodium arylsulfinates |
| title_fullStr | Palladium-catalyzed stereoselective C-glycosylation of glycals with sodium arylsulfinates |
| title_full_unstemmed | Palladium-catalyzed stereoselective C-glycosylation of glycals with sodium arylsulfinates |
| title_short | Palladium-catalyzed stereoselective C-glycosylation of glycals with sodium arylsulfinates |
| title_sort | palladium catalyzed stereoselective c glycosylation of glycals with sodium arylsulfinates |
| topic | DRNTU::Science::Chemistry::Organic chemistry |
| url | https://hdl.handle.net/10356/106693 http://hdl.handle.net/10220/25083 http://dx.doi.org/10.1002/ejoc.201403550 |
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