Efficient Synthesis of Pyrimidine-Nucleoside Monophosphates from H-Phosphonates

Jian Sun; Shan Shan Gong; Qi Sun

doi:10.4028/www.scientific.net/AMR.1023.87

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HomeAdvanced Materials ResearchAdvanced Materials Research Vol. 1023Efficient Synthesis of Pyrimidine-Nucleoside...

Efficient Synthesis of Pyrimidine-Nucleoside Monophosphates from H-Phosphonates

Abstract:

Two natural pyrimidine-nucleoside 5′-monophosphates have been synthesized from the corresponding nucleoside 5′-H-phosphonate monoesters via a one-pot reaction in high yields. ³¹P NMR tracing experiments revealed that after H₂O was added, iodophosphate intermediates were hydrolyzed immediately to generate nucleoside 5′-monophosphates almost quantitatively. Unlike the reaction in pyridine, the iodine oxidation reaction in DMF followed by immediate hydrolysis formed only a very small amount of dinucleoside diphosphate self-condensation byproduct.

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Periodical:

Advanced Materials Research (Volume 1023)

Pages:

87-90

DOI:

https://doi.org/10.4028/www.scientific.net/AMR.1023.87

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Online since:

August 2014

Authors:

Jian Sun, Shan Shan Gong, Qi Sun*

Keywords:

H-Phosphonate, Iodine, Nucleoside Monophosphate, Oxidation, Pyrimidine

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* - Corresponding Author

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