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Syntheses and properties of pterin ribonucleosides

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2008

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Pfadler, Werner

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https://doi.org/10.3998/ark.5550190.0010.309
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Arkivoc. Arkat. 2008(3), pp. 95-114. ISSN 1551-7012. eISSN 1551-7004. Available under: doi: 10.3998/ark.5550190.0010.309

Zusammenfassung

Several pterin derivatives (1-8) have been ribosylated in form of their trimethylsilyl derivatives (9) with 1-bromo-(10) and 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (11) under the catalysis of HgO/HgBr 2 , BF3 -etherate and trimethylsilyl triflate, respectively. Mixtures of the N-1- (19-25) and N-3-ribofuranosides (12-18) which are difficult to be separated were obtained. Debenzoylation by the Zemplen method led to the free pterin-nucleosides (28-30). A second approach starting from 2-methylthio-4(3H)pteridinones (31-33) gave again mixtures of the N-1-(35-37) and N-3-ribonucleosides (38-40). The 2-methylthio function in 35-37 can easily be substituted by various amines leading after subsequently debenzoylation to the N-2- substituted pterin-ribonucleosides (41-50). The structural assignments were based on comparisons of the UV spectra with the corresponding N-methyl substituted model substances. 1 H-NMR-spectra functioned as additional structural proof.

Zusammenfassung in einer weiteren Sprache

Fachgebiet (DDC)
540 Chemie

Schlagwörter

Pterin ribosylations, silyl methods, UV comparisons, pK -determinations

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ISO 690PFADLER, Werner, Wolfgang PFLEIDERER, 2008. Syntheses and properties of pterin ribonucleosides. In: Arkivoc. Arkat. 2008(3), pp. 95-114. ISSN 1551-7012. eISSN 1551-7004. Available under: doi: 10.3998/ark.5550190.0010.309
BibTex
@article{Pfadler2008Synth-58595,
  year={2008},
  doi={10.3998/ark.5550190.0010.309},
  title={Syntheses and properties of pterin ribonucleosides},
  number={3},
  issn={1551-7012},
  journal={Arkivoc},
  pages={95--114},
  author={Pfadler, Werner and Pfleiderer, Wolfgang}
}
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    <dcterms:abstract xml:lang="eng">Several pterin derivatives (1-8) have been ribosylated in form of their trimethylsilyl derivatives (9) with 1-bromo-(10) and 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose (11) under the catalysis of HgO/HgBr 2 , BF3 -etherate and trimethylsilyl triflate, respectively. Mixtures of the N-1- (19-25) and N-3-ribofuranosides (12-18) which are difficult to be separated were obtained. Debenzoylation by the Zemplen method led to the free pterin-nucleosides (28-30). A second approach starting from 2-methylthio-4(3H)pteridinones (31-33) gave again mixtures of the N-1-(35-37) and N-3-ribonucleosides (38-40). The 2-methylthio function in 35-37 can easily be substituted by various amines leading after subsequently debenzoylation to the N-2- substituted pterin-ribonucleosides (41-50). The structural assignments were based on comparisons of the UV spectra with the corresponding N-methyl substituted model substances. 1 H-NMR-spectra functioned as additional structural proof.</dcterms:abstract>
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