Synthesis of novel glycophanes derived from glucuronic acid by ring closing alkene and alkyne metathesis

Carbohydrate Research
Dearbhla Doyle, Paul V Murphy


Cyclophanes and their analogues are of interest in bioactive molecule development and in biomimetic, supramolecular and materials chemistry. Novel hybrids of sugars and cyclophanes (glycophanes) have been prepared via the coupling of alkenyl and alkynyl glucopyranosiduronic acids with phenylene-1,4-diamine and xylene-1,4-diamine and subsequent intramolecular metathesis. Structural studies showed that the geometric arrangements of the sugar groups in the macrocycles containing secondary amides differ from those in macrocycles that contain tertiary amides. This is due to the amides adopting different configurational preferences. The compounds had low solubility in water, precluding an investigation of their recognition phenomena in this medium.


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Nov 12, 2009·Chemical Communications : Chem Comm·Hongxue HuangXinmiao Liang
Oct 23, 2018·Chemistry : a European Journal·Henrike Ehrhorn, Matthias Tamm
Jan 29, 2013·Angewandte Chemie·Alois Fürstner

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