Nucleophilic opening of epoxyazepanes: expanding the family of polyhydroxyazepane-based glycosidase inhibitors

Organic & Biomolecular Chemistry
Hongqing LiYves Blériot

Abstract

A range of new tetra- and pentahydroxylated seven-membered iminoalditols has been efficiently synthesized from epoxyazepane precursors via nucleophilic opening with hydride or oxygenated species and subsequent hydrogenolysis. One tetrahydroxylated azepane, a ring homologue of deoxymannojirimycin, displays a selective and fairly good inhibition of alpha-L-fucosidase.

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Citations

Dec 21, 2006·Chemical Communications : Chem Comm·Hongqing LiYves Blériot
Jun 27, 2015·Organic & Biomolecular Chemistry·Stéphane SalamoneHenrik H Jensen
Jan 12, 2008·Chembiochem : a European Journal of Chemical Biology·Hongqing LiYves Blériot
May 10, 2013·Organic & Biomolecular Chemistry·Alpesh Ramanlal PatelFei Liu
Aug 24, 2010·Journal of Computational Chemistry·Ahmed Mutanabbi AbdulaMutasem O Taha
Oct 2, 2009·The Journal of Organic Chemistry·Gérald EnderlinYves Chapleur
Mar 6, 2013·The Journal of Organic Chemistry·Wen-Bo ZhaoChu-Yi Yu
Oct 21, 2014·Organic Letters·Yves BlériotMatthieu Sollogoub
Aug 25, 2011·Bioorganic & Medicinal Chemistry·Peter A BurlandAndrea Turkson

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