Approaches to intramolecular sialylation. 2. Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group |
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| Authors: | L. O. Kononov A. M. Shpirt Y. Ito T. Ogawa |
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| Affiliation: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation;(2) Higher Chemical College of the Russian Academy of Sciences, 9 Miusskaya pl., 125047 Moscow, Russian Federation;(3) Institute of Physical and Chemical Research (RIKEN), Hirosawa 2-1, Wako-shi, Saitama, 351-01, Japan |
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| Abstract: | Various approaches to the synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid (Neu5Ac) containing an unprotected carboxy group starting from the corresponding methyl esters were comparatively studied. One-step demethylation of methyl thioglycoside (LiI, Py, reflux) proceeded inefficiently in contrast to the analogous smooth reaction of phenyl thioglycoside. An indirect route to derivatives with a free carboxy group involving saponification followed by acetylation of hydroxy groups proved to be more efficient for methyl  -thioglycoside of Neu5Ac. |
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| Keywords: | sialic acids N-acetylneuraminic acid thioglycosides monosaccharides NMR spectroscopy |
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