Synthesis of a nonavalent mannoside glycodendrimer based on pentaerythritol.
[reaction: see text] 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.[1]References
- Synthesis of a nonavalent mannoside glycodendrimer based on pentaerythritol. Al-Mughaid, H., Grindley, T.B. J. Org. Chem. (2006) [Pubmed]
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