Synthesis of cycloSal-(Glycopyranosyl-6)-Phosphates as activated Sugar Phosphates

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Autor/in:
Erscheinungsjahr:
2013
Medientyp:
Text
Schlagworte:
  • Nucleosides
  • Nucleotides
  • Cap analogs
  • Oligonucleotides
  • DNA
  • Nucleosides
  • Nucleotides
  • Cap analogs
  • Oligonucleotides
  • DNA
Beschreibung:
  • The synthesis of cycloSal-masked glycopyranosyl phosphates demands suitably protected precursors. A highly regioselective strategy for the preparation of cycloSal-(1,2,3,4-tetra-O-acetylglycopyranosyl-6)-phosphates was developed. Intermediate introduction of the Fmoc-group allowed the isolation of the 1,2,3,4-tetra-O-acetyl glycopyranoses to be skipped, thus, no isomerization occurred. Glycopyranoses were first converted into the 6-O-TBDMS-1,2,3,4-tetra-O-acetyl derivatives then, in a one-pot reaction, the silyl ether was cleaved and the resulting 1,2,3,4-tetra-O-acetyl glycopyranoses were trapped with Fmoc-chloride. In this exchange of protecting groups no acetyl group migration occurred. The 6-O-Fmoc-protected intermediates were selectively converted into the cycloSal-masked glycopyranosyl phosphates in a one-pot reaction. Finally, the reactivity of these activated glycopyranosyl-6-phosphates was demonstrated in the synthesis of 1,6-diglycopyranosyl-phosphates.
Lizenz:
  • info:eu-repo/semantics/restrictedAccess
Quellsystem:
Forschungsinformationssystem der UHH

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Quelldatensatz
oai:www.edit.fis.uni-hamburg.de:publications/2a972d2a-e0a8-47fd-8e21-6066c13caf63