54340-91-9Relevant articles and documents
Oxidation of Methyl Trimethylsilyl Ketene Acetals to α-Hydroxyesters with Urea Hydrogen Peroxide Catalyzed by Methyltrioxorhenium
Stankovic, Sasa,Espenson, James H.
, p. 5528 - 5530 (2007/10/03)
In the presence of catalytic amounts of MTO, methyltrioxorhenium, methyl trimethylsilyl ketene acetals are oxidized with urea hydrogen peroxide to afford α-hydroxy and α-siloxy esters. On treatment with potassium fluoride, the α-hydroxy esters are obtained in high yields.
4-Hydroxynon-2-enal, a cytotoxic lipid peroxidation product, and its C5- analog 4-hydroxypent-2-enal: Enantioselective synthesis and stereoanalysis
Bringmann,Gassen,Lardy
, p. 10245 - 10252 (2007/10/02)
A stereoselective synthesis of the lipid peroxidation products 4- hydroxypent-2-enal (1a) and 4-hydroxynon-2-enal (1b) in high optical purity is presented. The configuration of 1a and b was established by Ru(III)- catalyzed oxidative degradation and subsequent stereoanalysis of the resulting α-hydroxy acids. It was demonstrated that 1a is configuratively stable under physiological conditions.
Synthesis of S-Methyl 2-Hydrxyalkanethioates, 2-Hydroxyalkanoic Acids and Related Compounds via the Addition Reaction of Tris(methylthio)methanide Ion to Alkanals
Orito, Kazuhiko,Seki, Yoshikatsu,Suginome, Hiroshi,Iwadare, Tsukasa
, p. 2013 - 2017 (2007/10/02)
In connection with the studies on biological activities on myrmicacin and related compounds, the synthetic method for 2-hydroxyalkanoic acids and the corresponding 1,2-diols was studied.The addition reaction of tris(methylthio)methyllithium to the aldehydes (propanal-dodecanal) gave the corresponding 1,1,-tris(methylthio)-2-alkanols 1a-j.Treatment of 1 with mercury(II) chloride-mercury(II) oxide in water-acetone afforded S-methyl 2-hydroxyalkanethioates 2a-j, and in methanol methyl 2-hydroxyalkanoates 3c-j were obtained.Reduction of the thioates 2 with lithium aluminium hydride gave 1,2-diols 4c-j and saponification produced the corresponding 2-hydroxyalkanoic acids 5c-j.