Methyl 5-Deoxy-α and β-D-Xylofuranosides |
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| Authors: | Jitka Moravcová Jindra Čapková Jan Staněk Ivan Raich |
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| Institution: | Department of Chemistry of Natural Compounds , Institute of Chemical Technology , Technická 5, 166 28, Prague, Czech Republic |
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| Abstract: | Abstract Synthesized from D-xylose, methyl 5-deoxy-α-D-xylofuranoside (1) and methyl 5-deoxy-β-D-xylofuranoside (2) were obtained in overall yields of 24 and 26 %, respectively. The key step in the synthesis was the separation of an anomeric mixture on a strong anion exchanger in OH? form. NMR data and mass spectra of title compounds 1, 2, methyl 2,3-di-O-acetyl-5-deoxy-α-D-xylofuranoside (3), and methyl 2,3-di-O-acetyl-5-deoxy-β-D-xylofuranoside (4) are discussed. The conformations of 1 and 2 were established from the best fit between calculated and experimental coupling constants using Karplus equation. |
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