The Synthesis and Structure of Selected Methyl (3,4-Di-O-acetyl-2-deoxy-2-hydroxyimino-d-arabino-hexopyranosid)urontes |
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Authors: | Zygfryd Smiatacz Iwona Chrzczanowicz Henryk Myszka Pawe? Dokurno |
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Institution: | Department of Chemistry , University of Gdańsk , 80-952, Gdańsk, Sobieskiego, 18, Poland |
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Abstract: | Abstract Dimeric methyl (3,4-di-O-acetyl-2-deoxy-2-nitroso-α-d-glucopyranosyl chloride)uronate (1) reacts with nucleophiles such as: ethanol, pyrazole, methyl N-tert-butyloxycarbonyl-L-serinate to give corresponding glycosides. The stereospecifity of the glycosidation reaction depends mainly on the employed nucleophile. The configuration and conformation of the obtained glycosides were established on the basis of 1H NMR and polarimetric data, and additionally the structure of 1-(methyl 3,4-di-O-acetyl-2-deoxy-2-(Z)-hydroxyimino-α-d-arabino-hexopyranosyluronate)pyrazole (6), was supported by X-ray diffraction data. |
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