Synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation catalyzed by 2-methyl-5-phenylbenzoxazolium perchlorate |
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Authors: | Hiroshi Shirouzu Hiroki MoritaMasaki Tsukamoto |
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Affiliation: | Graduate School of Information Science, Nagoya University, Chikusa, Nagoya 464-8601, Japan |
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Abstract: | Several acidic azolium salts prepared from oxazole, thiazole, and imidazole derivatives were investigated as catalysts in N-glycosylation reaction using a silylated modified pyrimidine and an acylated ribose or glucose to afford the corresponding pyrimidine nucleoside. Among the salts, 2-methyl-5-phenylbenzoxazolium perchlorate showed the highest catalytic activity. This salt is a nonhygroscopic crystalline compound that shows higher activity than the frequently used trimethylsilyl triflate. Reactions with this salt can be conducted in gram scales. |
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Keywords: | N-Glycosylation Pyrimidine nucleoside Brø nsted acid Oxazolium perchlorate Catalysis |
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