Synthesis of a nonavalent mannoside glycodendrimer based on pentaerythritol

J Org Chem. 2006 Feb 17;71(4):1390-8. doi: 10.1021/jo052045u.

Abstract

A nonavalent glycodendrimer bearing terminal alpha-d-mannopyranoside units has been synthesized with a convergent approach. Terminal trivalent mannoside dendrons bearing p-halophenyl ethers were prepared by glycosylation of pentaerythritol derivatives having three 2-hydroxyethyl ether substituents. Two efficient routes were developed for the synthesis of the pentaerythritol-based core (17), which has three terminal propargyl ethers. Conditions were found under which the triple Sonogashira coupling reaction of the dendron and the tri-O-propargyl ether (17) proceeded efficiently. The product was deprotected and it and precursors were fully characterized by NMR spectroscopy and FT-ICR mass spectrometry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Dendrimers / chemical synthesis*
  • Ethers / chemistry
  • Glycosylation
  • Magnetic Resonance Spectroscopy
  • Mannosides / chemical synthesis*
  • Mass Spectrometry
  • Propylene Glycols / chemistry*

Substances

  • Dendrimers
  • Ethers
  • Mannosides
  • Propylene Glycols
  • pentaerythritol