Chemistry Publications


Unusual C7- versus Normal 5’-O-Dimethoxytritylation of 6-Arylpyrrolocytidine Analogs

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The Journal of Organic Chemistry

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DOI: 10.1021/acs.joc.6b01584


Fluorescent deoxynucleosides possessing the modified bases 6-(2-benzo[b]furyl)- and 6-(2-furyl)-pyrrolocytosine (BFpC and FpC) have been synthesized along with the quencher nucleosides possessing 6-{4-[(4-dimethylamino)azo]phenylpyrrolocytosine (DABCYLpC) and 6-(p-nitrophenyl)pyrrolocytosine (p-NO2-PhpC) nucleobase analogs. Standard treatment of BFpC, FpC, DABCYLpC and p-NO2-PhpC with dimethoxytrityl chloride (DMT-Cl) led to the unusual substitution on the C7 of the pyrrolocytosine skeleton. The desired 5’-O-DMT protected nucleoside analogs were synthesized from suitably protected 5’-O-DMT cytidines. Subsequent phosphitylation smoothly afforded BFpC-, FpC-, DABCYLpC- and p-NO2-PhpC-derived monomers suitable for standard oligonucleotide synthesis.


Mojmir Suchy, Christie Ettles, James A. Wisner, Augusto Matarazzo, and Robert H. E. Hudson

J. Org. Chem., Just Accepted Manuscript

DOI:10.1021/acs.joc.6b01584 Publication Date (Web): August 16, 2016

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