125848-29-5Relevant academic research and scientific papers
Ferrier rearrangement promoted by an electrochemically generated zirconium catalyst
Stevanovi?, Dragana,Pejovi?, Anka,Damljanovi?, Ivan,Mini?, Aleksandra,Bogdanovi?, Goran A.,Vuki?evi?, Mirjana,Radulovi?, Niko S.,Vuki?evi?, Rastko D.
, p. 111 - 121 (2015)
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.
A Route to Glycals in the Allal and Gulal Series: Synthesis of the Thiosugar of Esperamicin A1
Wittman, Mark D.,Halcomb, Randall L.,Danishefsky, Samuel J.,Golik, Jerzy,Vyas, Dolatrai
, p. 1979 - 1981 (2007/10/02)
Axial anomeric sulfoxides generated via thiophenol Ferrier rearrangement of glucal and galactal derivatives are used to synthesize glycals of the gulal and allal series.An application of the method led to the synthesis of the esperamicin thiosugar, thereb
