Synthesis of Glycosides with 4-(4-Hydroxyphenyl)-1,2,3-thia- and -selenadiazole Aglycones
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Glycosylation of 4-(4-hydroxyphenyl)-1,2,3-thia(selena)diazoles with 1-α-bromo-2,3,4,6-tetra-O-acetyl-D-glucopyranose, 1-α-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose, and 1-α-bromo-2,3,5-tri-O-acetyl-D-xylopyranose under the conditions of interphase catalysis has afforded the corresponding acetylated glycosides. An alternative pathway of selenadiasole glycosides synthesis from semicarbazones of 1-β-O-(4-acetylphenyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose, -2,3,4,6-tetra-O-acetyl-D-galactopyranose, and -2,3,5-tri-O-acetyl-D-xylopyranose via oxidation with selenium dioxide has been elaborated.
Keywordsglycosylation Könnigs-Knorr reaction interphase catalysis 1,2,3-thiadiazoles semicarbazides 1,2,3-selenadiazoles
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This study was carried out in the scope of the basic part of state project of Ministry of Education and Science of the Russian Federation, project no 4.5554.2017/8.9, using the equipment of the Resource Centers of St. Petersburg State University “Methods of analysis of composition of substance” and “X-ray diffraction methods of investigation”
- 2.Jadhav, A.A., Dhanwe, V.P., Joshi, P.G., and Khanna, P.K., Cogent Chem., 2016, no. 2, p. 1144670. doi https://doi.org/10.1080/23312009.2016.11444670
- 3.Way2Drug.com©2011-2018.Version 2.0.Google Scholar
- 5.Dess, D., Kleine, H.P., Weinberg, D.V, Kaufman, R.J., and Sidhu, R.S., Synthesis, 1981, no. 11, p. 883. doi https://doi.org/10.1055/s-1981-29361
- 6.Caplin, A., J. Chem. Soc. Perkin Trans. 1, 1974, p. 30. doi https://doi.org/10.1039/P19740000030