Efficient Synthesis Of Alkyl And Aryl 2,3-Unsaturated Glycopyranosides via Ferrier Rearrangement
The reactions of 3,4,6-tri-O-acetyl-D-glucal with phenolic and aliphatic alcohol in various Lewis acid catalysts (namely La(NO3)3.6H2O, InCl3, ZnCl2 and BF3•OEt2) have furnished the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides via Ferrier rearrangement. BF3•OEt2 showed the best Lewi...
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| Language: | English |
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1112-9867
2011
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| Online Access: | http://ir.unimas.my/id/eprint/15583/ http://ir.unimas.my/id/eprint/15583/1/Efficient%20Synthesis%20Of%20Alkyl%20And%20Aryl%202%2C3%20%28abstract%29.pdf |
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| author | Dayang Halimatulzahrah, bt. Abang Kamaluddin Zainab, Ngaini |
| author_facet | Dayang Halimatulzahrah, bt. Abang Kamaluddin Zainab, Ngaini |
| author_sort | Dayang Halimatulzahrah, bt. Abang Kamaluddin |
| building | UNIMAS Institutional Repository |
| collection | Online Access |
| description | The reactions of 3,4,6-tri-O-acetyl-D-glucal with phenolic and aliphatic alcohol in various Lewis acid catalysts (namely La(NO3)3.6H2O, InCl3, ZnCl2 and BF3•OEt2) have furnished the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides via Ferrier rearrangement. BF3•OEt2 showed the best Lewis acids catalysts with excellent yields and minimum reaction times. The reactions performed in CH3CN gave better yields and shorter reaction times compared to CH2Cl2. The electron withdrawing properties of aromatic ring resulting lower yields of aryl 2,3-unsaturated glycopyranosides compared to alkyl 2,3-unsaturated glycopyranosides under this condition. This study is significant in the preparation of O-glycosides via Ferrier rearrangement |
| first_indexed | 2025-11-15T06:46:44Z |
| format | Article |
| id | unimas-15583 |
| institution | Universiti Malaysia Sarawak |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-15T06:46:44Z |
| publishDate | 2011 |
| publisher | 1112-9867 |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | unimas-155832017-03-15T15:29:19Z http://ir.unimas.my/id/eprint/15583/ Efficient Synthesis Of Alkyl And Aryl 2,3-Unsaturated Glycopyranosides via Ferrier Rearrangement Dayang Halimatulzahrah, bt. Abang Kamaluddin Zainab, Ngaini QD Chemistry The reactions of 3,4,6-tri-O-acetyl-D-glucal with phenolic and aliphatic alcohol in various Lewis acid catalysts (namely La(NO3)3.6H2O, InCl3, ZnCl2 and BF3•OEt2) have furnished the corresponding alkyl and aryl 2,3-unsaturated glycopyranosides via Ferrier rearrangement. BF3•OEt2 showed the best Lewis acids catalysts with excellent yields and minimum reaction times. The reactions performed in CH3CN gave better yields and shorter reaction times compared to CH2Cl2. The electron withdrawing properties of aromatic ring resulting lower yields of aryl 2,3-unsaturated glycopyranosides compared to alkyl 2,3-unsaturated glycopyranosides under this condition. This study is significant in the preparation of O-glycosides via Ferrier rearrangement 1112-9867 2011 Article PeerReviewed text en http://ir.unimas.my/id/eprint/15583/1/Efficient%20Synthesis%20Of%20Alkyl%20And%20Aryl%202%2C3%20%28abstract%29.pdf Dayang Halimatulzahrah, bt. Abang Kamaluddin and Zainab, Ngaini (2011) Efficient Synthesis Of Alkyl And Aryl 2,3-Unsaturated Glycopyranosides via Ferrier Rearrangement. Journal of Fundamental Sciences, 7 (2). pp. 93-96. ISSN 1823-626X https://www.researchgate.net/publication/291336553_Efficient_Synthesis_Of_Alkyl_And_Aryl_23-Unsaturated_Glycopyranosides_via_Ferrier_Rearrangement |
| spellingShingle | QD Chemistry Dayang Halimatulzahrah, bt. Abang Kamaluddin Zainab, Ngaini Efficient Synthesis Of Alkyl And Aryl 2,3-Unsaturated Glycopyranosides via Ferrier Rearrangement |
| title | Efficient Synthesis Of Alkyl And Aryl 2,3-Unsaturated Glycopyranosides via Ferrier Rearrangement |
| title_full | Efficient Synthesis Of Alkyl And Aryl 2,3-Unsaturated Glycopyranosides via Ferrier Rearrangement |
| title_fullStr | Efficient Synthesis Of Alkyl And Aryl 2,3-Unsaturated Glycopyranosides via Ferrier Rearrangement |
| title_full_unstemmed | Efficient Synthesis Of Alkyl And Aryl 2,3-Unsaturated Glycopyranosides via Ferrier Rearrangement |
| title_short | Efficient Synthesis Of Alkyl And Aryl 2,3-Unsaturated Glycopyranosides via Ferrier Rearrangement |
| title_sort | efficient synthesis of alkyl and aryl 2,3-unsaturated glycopyranosides via ferrier rearrangement |
| topic | QD Chemistry |
| url | http://ir.unimas.my/id/eprint/15583/ http://ir.unimas.my/id/eprint/15583/ http://ir.unimas.my/id/eprint/15583/1/Efficient%20Synthesis%20Of%20Alkyl%20And%20Aryl%202%2C3%20%28abstract%29.pdf |