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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Main Authors: Dayang Halimatulzahrah, bt. Abang Kamaluddin, Zainab, Ngaini
Format: E-Article
Language:English
Published: 1112-9867 2011
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Online Access:http://ir.unimas.my/id/eprint/15583/1/Efficient%20Synthesis%20Of%20Alkyl%20And%20Aryl%202%2C3%20%28abstract%29.pdf
http://ir.unimas.my/id/eprint/15583/
https://www.researchgate.net/publication/291336553_Efficient_Synthesis_Of_Alkyl_And_Aryl_23-Unsaturated_Glycopyranosides_via_Ferrier_Rearrangement
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spelling my.unimas.ir.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 E-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
institution Universiti Malaysia Sarawak
building Centre for Academic Information Services (CAIS)
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaysia Sarawak
content_source UNIMAS Institutional Repository
url_provider http://ir.unimas.my/
language English
topic QD Chemistry
spellingShingle QD Chemistry
Dayang Halimatulzahrah, bt. Abang Kamaluddin
Zainab, Ngaini
Efficient Synthesis Of Alkyl And Aryl 2,3-Unsaturated Glycopyranosides via Ferrier Rearrangement
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
format E-Article
author Dayang Halimatulzahrah, bt. Abang Kamaluddin
Zainab, Ngaini
author_facet Dayang Halimatulzahrah, bt. Abang Kamaluddin
Zainab, Ngaini
author_sort Dayang Halimatulzahrah, bt. Abang Kamaluddin
title 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_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_sort efficient synthesis of alkyl and aryl 2,3-unsaturated glycopyranosides via ferrier rearrangement
publisher 1112-9867
publishDate 2011
url http://ir.unimas.my/id/eprint/15583/1/Efficient%20Synthesis%20Of%20Alkyl%20And%20Aryl%202%2C3%20%28abstract%29.pdf
http://ir.unimas.my/id/eprint/15583/
https://www.researchgate.net/publication/291336553_Efficient_Synthesis_Of_Alkyl_And_Aryl_23-Unsaturated_Glycopyranosides_via_Ferrier_Rearrangement
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score 13.211869