Synthesis of a Nonavalent Mannoside Glycodendrimer Based on Pentaerythritol

A nonavalent glycodendrimer bearing terminal α-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...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-02, Vol.71 (4), p.1390-1398
Main Authors: Al-Mughaid, Hussein, Grindley, T. Bruce
Format: Article
Language:English
Subjects:
Chemistry
Dendrimers - chemical synthesis
Ethers - chemistry
Exact sciences and technology
Glycosylation
Magnetic Resonance Spectroscopy
Mannosides - chemical synthesis
Mass Spectrometry
Organic chemistry
Propylene Glycols - chemistry
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Summary:A nonavalent glycodendrimer bearing terminal α-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo052045u