Citric acid mediated simple and stereoselective synthesis of o-linked glycosides by Ferrier rearrangement
A simple and environment-friendly citric acid-mediated synthesis of glycosides has been reported using Ferrier-rearrangement. Using this protocol, synthesis of several glycosides including pseudo disaccharides was prepared. Citric acid was successfully employed for the synthesis of glycosides from D...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Elsevier
2022-01-01
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| Series: | Results in Chemistry |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715622000662 |
| _version_ | 1811296769139539968 |
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| author | P.I. Ramesh Mohamad Saif Ali Subhash Ghosh Madhu Babu Tatina |
| author_facet | P.I. Ramesh Mohamad Saif Ali Subhash Ghosh Madhu Babu Tatina |
| author_sort | P.I. Ramesh |
| collection | DOAJ |
| description | A simple and environment-friendly citric acid-mediated synthesis of glycosides has been reported using Ferrier-rearrangement. Using this protocol, synthesis of several glycosides including pseudo disaccharides was prepared. Citric acid was successfully employed for the synthesis of glycosides from D-glucal, L-rhamnal, D-xylal and D-galactal with various alcohols to give a broad range of glycosides in up to 80% yields with α-isomer as major product under mild reaction conditions. |
| first_indexed | 2024-04-13T05:53:23Z |
| format | Article |
| id | doaj.art-c684077e5d4640dcbcbea40188cac820 |
| institution | Directory Open Access Journal |
| issn | 2211-7156 |
| language | English |
| last_indexed | 2024-04-13T05:53:23Z |
| publishDate | 2022-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj.art-c684077e5d4640dcbcbea40188cac8202022-12-22T02:59:41ZengElsevierResults in Chemistry2211-71562022-01-014100347Citric acid mediated simple and stereoselective synthesis of o-linked glycosides by Ferrier rearrangementP.I. Ramesh0Mohamad Saif Ali1Subhash Ghosh2Madhu Babu Tatina3Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, IndiaDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, IndiaDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201 002, IndiaDepartment of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Corresponding author.A simple and environment-friendly citric acid-mediated synthesis of glycosides has been reported using Ferrier-rearrangement. Using this protocol, synthesis of several glycosides including pseudo disaccharides was prepared. Citric acid was successfully employed for the synthesis of glycosides from D-glucal, L-rhamnal, D-xylal and D-galactal with various alcohols to give a broad range of glycosides in up to 80% yields with α-isomer as major product under mild reaction conditions.http://www.sciencedirect.com/science/article/pii/S2211715622000662Ferrier-glycosylationOrgano-mediatedCitric acidO-linked pseudo-glycosides |
| spellingShingle | P.I. Ramesh Mohamad Saif Ali Subhash Ghosh Madhu Babu Tatina Citric acid mediated simple and stereoselective synthesis of o-linked glycosides by Ferrier rearrangement Results in Chemistry Ferrier-glycosylation Organo-mediated Citric acid O-linked pseudo-glycosides |
| title | Citric acid mediated simple and stereoselective synthesis of o-linked glycosides by Ferrier rearrangement |
| title_full | Citric acid mediated simple and stereoselective synthesis of o-linked glycosides by Ferrier rearrangement |
| title_fullStr | Citric acid mediated simple and stereoselective synthesis of o-linked glycosides by Ferrier rearrangement |
| title_full_unstemmed | Citric acid mediated simple and stereoselective synthesis of o-linked glycosides by Ferrier rearrangement |
| title_short | Citric acid mediated simple and stereoselective synthesis of o-linked glycosides by Ferrier rearrangement |
| title_sort | citric acid mediated simple and stereoselective synthesis of o linked glycosides by ferrier rearrangement |
| topic | Ferrier-glycosylation Organo-mediated Citric acid O-linked pseudo-glycosides |
| url | http://www.sciencedirect.com/science/article/pii/S2211715622000662 |
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