Trimethylsilyl derivatives of N-Boc-cytosine and their effect on I2-mediated nucleosidation of O-MTM ethers |
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| Authors: | Yumei HuangSubhakar Dey Philip Garner |
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| Institution: | Department of Chemistry, Case Western Reserve University, Cleveland, OH 44106-7078, USA |
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| Abstract: | Mono- and bis(trimethylsilyl) derivatives of N4-Boc-cytosine were synthesized and characterized by 1H NMR. Only the mono(trimethylsilyl)-N4-Boc-cytosine participates in the iodine-mediated nucleosidation of N-Fmoc-O-methylthiomethyl serine benzyl ester to produce the cytosine nucleoamino acid, while the bis(trimethylsilyl) derivative failed to give any product. A tentative mechanistic explanation is proposed. |
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| Keywords: | silylation N4-Boc-cytosine NMR nucleosidation |
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