Efficient synthesis of 5′-O(N)-carbamyl and -polycarbamyl nucleosides |
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Authors: | Jadd R Shelton Matt A Peterson |
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Institution: | Department of Chemistry and Biochemistry, Brigham Young University, Provo, UT, United States |
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Abstract: | A simple and efficient method for the preparation of 5′-O(N)-carbamyl and 5′-O(N)-polycarbamyl nucleoside derivatives is reported. The method consisted of treatment of 2′,3′-O-protected purine (Ado, Ino) or pyrimidine nucleosides (Thd, Urd) with trichloroacetylisocyanate, followed by cleavage of the trichloroacetyl moiety by silica-gel promoted methanolysis during column chromatography. Iterative application of this method gave mono, di, and tricarbamyl derivatives in good to excellent yields (ave = 80%). |
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Keywords: | 5&prime -O(N)-Carbamyl nucleosides 5&prime -O(N)-Polycarbamyl nucleosides Polycarbamylation 5&prime -Modified nucleosides |
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