Convenient synthesis of N-isobutyryl-2′-O-methyl guanosine by efficient alkylation of O-trimethylsilylethyl-3′,5′-di-tert-butylsilanediyl guanosine |
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Authors: | Ivan Zlatev |
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Institution: | Institut des Biomolécules Max Mousseron UMR 5247 CNRS-UM1-UM2, Université Montpellier 2, CC1704, Place E. Bataillon, 34095 Montpellier Cedex 5, France |
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Abstract: | We present a novel route for the synthesis of N2-isobutyryl-2′-O-methyl guanosine, introducing 3′,5′-di-tert-butylsilyl and O6-trimethylsilylethyl groups as efficient protections during the 2′-O-methylation step with NaH/CH3I. These protections were then removed simultaneously in a single step with TBAF. The eight-step synthesis is easy to perform, employing convenient commercially available reagents; crude mixtures are of satisfying purity, so only three chromatography purifications were required. Title compound was obtained in 25% overall yield from guanosine. |
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Keywords: | Alkylation 2&prime -O-Methyl guanosine O6-Silyl protection |
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