Synthesis of Pyranonucleoside-6′-triphosphates through the cycloSal-Method

Link:
Autor/in:
Erscheinungsjahr:
2014
Medientyp:
Text
Schlagwort:
  • Nucleotides, Glycoconjugates, Carbohydrates, Phosphorylation, Medicinal chemistry
Beschreibung:
  • The high yielding synthesis of pyranonucleoside-6′-triphosphates by using the cycloSal-method is described. Synthesis of the activated cycloSal-pyranonucleoside-6′-phosphate triesters was achieved by applying a synthetic route that had been developed for the synthesis of cycloSal-(glycopyranosyl-6)-phosphates by us. The route involved regioselective 6′-tert-butyldimethylsilyl protection and exchange of the silyl protecting group by the fluorenylmethyloxycarbonyl (Fmoc) group. The 6′-Fmoc-protected derivatives were selectively converted into the cycloSal-triester. These were then very efficiently converted into triphosphates by a “titration-like” reaction with pyrophosphate. Simple purification by first ion exchange followed by reversed phase (RP) column chromatography afforded the triphosphates in very good yields.
Lizenz:
  • info:eu-repo/semantics/restrictedAccess
Quellsystem:
Forschungsinformationssystem der UHH

Interne Metadaten
Quelldatensatz
oai:www.edit.fis.uni-hamburg.de:publications/3749bcf0-8382-4c7e-8efd-bfc92d6b0edc