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Reaction of Acetyl Hypofluorite with Pyrimidines. Part 3. Synthesis, Stereochemistry, and Properties of 5-Fluoro-5,6-dihydropyrimidine Nucleosides

DOI: 10.1039/P19880002547

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2547 - 2554 (1988)

Update date:2022-08-04

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Authors:

Visser, Gerard W. M.Visser, Gerard W. M.

Herder, Renella E.Herder, Renella E.

Noordhuis, PaulNoordhuis, Paul

Zwaagstra, OeneZwaagstra, Oene

Herscheid, Jacobus D. M.Herscheid, Jacobus D. M.

Kanter, Frans J. J. deKanter, Frans J. J. de

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Article abstract of DOI:10.1039/P19880002547

The reaction of acetyl hypofluorite (AcOF) with unprotected uracil and cytosine nucleosides in acetic acid or water has been studied using (18)F as a tracer.For the nucleosides in general two cis-diastereoisomers of both the 6-acetoxy-5-fluoro and 5-fluoro-6-hydroxy adducts were obtained, (1)H n.m.r. analysis of which showed that they all possessed the anti-conformation.The 6-acetoxy-5-fluoroadducts in the uracil nucleosides showed a remarkable stability and appeared to be interesting versatile compounds.They could be converted into their hitherto unknown corresponding 5-fluoro-6-hydroxy-O6,5'-anhydrocyclouracil nucleosides.For the cytosine nucleosides the 6-acetoxy-5-fluoro adducts were not observed, while the other cytosine adducts were found to rapidly deaminate at C-4 in water yielding the corresponding uracil analogues.Interestingly, even within a pair of diastereoisomers different deamination rates were observed.

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Product name:Acetic acid (R)-3-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5,5-difluoro-6-imino-2-oxo-hexahydro-pyrimidin-4-yl ester

Cas No:119003-21-3

119003-21-3

R&D Labs maybe for 119003-21-3

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