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Ferrier Rearrangement Promoted by an Electrochemically Generated Zirconium Catalyst

Ferrier Rearrangement Promoted by an Electrochemically Generated Zirconium Catalyst

Dragana Stevanović, Anka Pejović, Ivan Damljanović, Aleksandra Minić, Goran A Bogdanović, Mirjana Vukićević, Niko S Radulović, Rastko D Vukićević

Carbohydr Res. 2015 Apr 30;407:111-21.

PMID: 25746956

Abstract:

In situ generated zirconium catalyst from a sacrificial zirconium anode was successfully applied to promote Ferrier rearrangement of 3,4,5-tri-O-acetyl-D-glucal and 6-deoxy-3,4-di-O-acetyl-L-glucal (3,4-di-O-acetyl-L-rhamnal) in the presence of three thiols and eleven thiophenols as nucleophiles. A simple constant current electrolysis (20 mA, 0.4 F mol(-1)) of an acetonitrile solution of lithium perchlorate (0.1 M) containing the corresponding glycal and S-nucleophiles, using a zirconium anode and a platinum cathode resulted in the successful synthesis of the corresponding 2,3-unsaturated peracetylated thioglycosides (with an average anomer ratio α/β=4.129 in the case of peracetylated D-glucal and 8.740 in the case of L-rhamnal). The same procedure proved to be appropriate in synthesizing dihydropyran derivatives ('C-glycosides') using allyltrimethylsilane as the nucleophile (only 'α-anomers' were obtained). All new compounds were fully characterized by spectral data, whereas single-crystal X-ray analysis was performed for two thioglycosides.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP2973866	Lithium thiophenolate solution		2973-86-6	Price

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