Novel 2,3-unsaturated O-glycosides containing an alkynyl function in their aglycones
This paper describes the synthesis of seven D-glucosides, 3a-g, and six D-galactosides, 4a-f, all containing an alkynyl function in their aglycones. The reaction was performed using dichloromethane as solvent in the presence of Montmorillonite K-10. The structure of all compounds were confirmed empl...
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| Language: | English |
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Elsevier
2025-01-01
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| Series: | Results in Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2211715624006878 |
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| author | Adriana C.N. de Melo Natália M. Bezerra Rajendra M. Srivastava Carlos Alberto de Simone |
| author_facet | Adriana C.N. de Melo Natália M. Bezerra Rajendra M. Srivastava Carlos Alberto de Simone |
| author_sort | Adriana C.N. de Melo |
| collection | DOAJ |
| description | This paper describes the synthesis of seven D-glucosides, 3a-g, and six D-galactosides, 4a-f, all containing an alkynyl function in their aglycones. The reaction was performed using dichloromethane as solvent in the presence of Montmorillonite K-10. The structure of all compounds were confirmed employing IR, 1H NMR and 13C NMR spectroscopic techniques. The aim was to study their conformational energies using ab initio Hartree Fock method with 6-31G as basis set. Two compounds, namely, (R)-(+)-3-butyn-2-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside, 3d, and (R)-(+)-3-butyn-2-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside, 4d, were subjected to X-ray diffraction analyses and their experimental values compared with the calculated values obtained by molecular orbital calculations. Our studies have found a good correlation between the two types of glycosides. |
| format | Article |
| id | doaj-art-9b329c1312e843c8a3fbd6f6293cfdf9 |
| institution | Kabale University |
| issn | 2211-7156 |
| language | English |
| publishDate | 2025-01-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Results in Chemistry |
| spelling | doaj-art-9b329c1312e843c8a3fbd6f6293cfdf92025-01-29T05:00:49ZengElsevierResults in Chemistry2211-71562025-01-0113101991Novel 2,3-unsaturated O-glycosides containing an alkynyl function in their aglyconesAdriana C.N. de Melo0Natália M. Bezerra1Rajendra M. Srivastava2Carlos Alberto de Simone3Departamento de Química Fundamental, Universidade Federal de Pernambuco, 50.740-540, Recife, PE BrazilDepartamento de Química Fundamental, Universidade Federal de Pernambuco, 50.740-540, Recife, PE BrazilDepartamento de Química Fundamental, Universidade Federal de Pernambuco, 50.740-540, Recife, PE Brazil; Corresponding author.Departamento de Química, Universidade Federal de Alagoas, Campus Universitário, Maceió 57000 Alagoas, Brazil; Departamento de Física e Informática, Instituto de Física de São Carlos, Universidade de São Paulo, USP, 13560-970, São Carlos, SP. BrazilThis paper describes the synthesis of seven D-glucosides, 3a-g, and six D-galactosides, 4a-f, all containing an alkynyl function in their aglycones. The reaction was performed using dichloromethane as solvent in the presence of Montmorillonite K-10. The structure of all compounds were confirmed employing IR, 1H NMR and 13C NMR spectroscopic techniques. The aim was to study their conformational energies using ab initio Hartree Fock method with 6-31G as basis set. Two compounds, namely, (R)-(+)-3-butyn-2-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside, 3d, and (R)-(+)-3-butyn-2-yl 4,6-di-O-acetyl-2,3-dideoxy-α-D-threo-hex-2-enopyranoside, 4d, were subjected to X-ray diffraction analyses and their experimental values compared with the calculated values obtained by molecular orbital calculations. Our studies have found a good correlation between the two types of glycosides.http://www.sciencedirect.com/science/article/pii/S22117156240068782,3-Unsaturated D-glucosides2,3-Unsaturated D-galactosidesNMR-Spectroscopy |
| spellingShingle | Adriana C.N. de Melo Natália M. Bezerra Rajendra M. Srivastava Carlos Alberto de Simone Novel 2,3-unsaturated O-glycosides containing an alkynyl function in their aglycones Results in Chemistry 2,3-Unsaturated D-glucosides 2,3-Unsaturated D-galactosides NMR-Spectroscopy |
| title | Novel 2,3-unsaturated O-glycosides containing an alkynyl function in their aglycones |
| title_full | Novel 2,3-unsaturated O-glycosides containing an alkynyl function in their aglycones |
| title_fullStr | Novel 2,3-unsaturated O-glycosides containing an alkynyl function in their aglycones |
| title_full_unstemmed | Novel 2,3-unsaturated O-glycosides containing an alkynyl function in their aglycones |
| title_short | Novel 2,3-unsaturated O-glycosides containing an alkynyl function in their aglycones |
| title_sort | novel 2 3 unsaturated o glycosides containing an alkynyl function in their aglycones |
| topic | 2,3-Unsaturated D-glucosides 2,3-Unsaturated D-galactosides NMR-Spectroscopy |
| url | http://www.sciencedirect.com/science/article/pii/S2211715624006878 |
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