Synthesis of Disaccharide Nucleosides by the O‐Glycosylation of Natural Nucleosides with Thioglycoside Donors |
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Authors: | Prof Shin Aoki Taketo Fukumoto Taiki Itoh Masayuki Kurihara Shigeto Saito Shin‐ya Komabiki |
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Institution: | 1. Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda 278‐8510 (Japan), Fax: (+81)?4‐7121‐3670;2. Center for Technologies against Cancer, Tokyo University of Science, 2641 Yamazaki, Noda 278‐8510 (Japan) |
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Abstract: | Disaccharide nucleosides constitute an important group of naturally‐occurring sugar derivatives. In this study, we report on the synthesis of disaccharide nucleosides by the direct O‐glycosylation of nucleoside acceptors, such as adenosine, guanosine, thymidine, and cytidine, with glycosyl donors. Among the glycosyl donors tested, thioglycosides were found to give the corresponding disaccharide nucleosides in moderate to high chemical yields with the above nucleoside acceptors using p‐toluenesulfenyl chloride (TolSCl) and silver triflate (AgOTf) as promoters. The interaction of these promoters with nucleoside acceptors was examined by 1H NMR spectroscopic experiments. |
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Keywords: | chemical glycosylation disaccharide nucleosides nucleosides O‐glycosylation thioglycoside |
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