Synthesis of a nonavalent mannoside glycodendrimer based on pentaerythritol.
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.
Department of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4J3 Canada.
Hussein
H
Al-Mughaid
T Bruce
TB
Grindley
D050091:Dendrimers / Q000138:chemical synthesis*; D004987:Ethers / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008362:Mannosides / Q000138:chemical synthesis*; D013058:Mass Spectrometry; D011409:Propylene Glycols / Q000737:chemistry*
D050091:Dendrimers; D004987:Ethers; D008362:Mannosides; D011409:Propylene Glycols; C008783:pentaerythritol