63991-86-6Relevant academic research and scientific papers
Synthesis of [14C]-Labelled glycidyl and glycerol ethers of aliphatic and aromatic alcohols.
Van Elburg,Ormskerk,De Kloe,Boogaard
, p. 147 - 167 (2007/10/03)
The synthesis of [14C]-labelled glycidyl ethers and the corresponding glycerol ethers is described for the monofunctional compounds 1-dodecanol and ortho-cresol and the bifunctional compounds 4,4'-dihydroxy-3,3',5,5'-tetramethyl biphenyl and 1,6-hexanediol. The synthesis is based on reaction between the alcohol and [U-14C]-epichlorohydrin. The aromatic compounds have been converted to the corresponding glycidyl ethers by using sodium hydroxide and the aliphatic compounds by using tin(IV) chloride as a catalyst. Thus radio-labelled glycidyl ethers were obtained in yields between 50-80, with a chemical purity of > 92 and a radiochemical purity of > 95 by HPLC. The specific activities of the glycidyl ethers were approximately 0.2 mCi/mmol for the monofunctional compounds and approximately 0.4 mCi/mmol for the bifunctional compounds.
Kinetic resolution of acyclic 1,2-diols using a sequential lipase- catalyzed transesterification in organic solvents
Theil,Weidner,Ballschuh,Kunath,Schick
, p. 388 - 393 (2007/10/02)
A method for the kinetic resolution of 3-(aryloxy)-1,2-propanediols rac- 1a-n without additional protection-deprotection steps using a lipase- catalyzed sequential transesterification with lipase amano PS has been developed. In the first step of this one-pot procedure the racemic 1,2-diols are acylated regioselectively at the primary hydroxy group without enantioselection. The subsequent acylation at the secondary hydroxy group of the formed primary monoacetate is responsible for high enantioselection. The enantioselectivity of this transformation depends significantly on the substitution pattern of the aryl ring and the organic solvent used. 3- (Aryloxy)-1,2-propanediols with substituents in the para-position show a much higher enantioselectivity than the corresponding derivatives with ortho- substituents. Among other substrates, the pharmaceuticals Mephenesin, Guaifenesin, and Chlorphenesin have been resolved. The replacement of the aryloxy by an alkyl substituent causes a dramatic decrease of enantioselectivity.
Kinetic Resolution of rac-3-(2-Methylphenoxy)propane-1,2-diol (Mephenesin) by Sequential Lipase-Catalyzed Transesterification
Theil, Fritz,Ballschuh, Sibylle,Kunath, Annamarie,Schick, Hans
, p. 1031 - 1034 (2007/10/02)
The kinetic resolution of rac-3-(2-methylphenoxy)propane-1,2-diol (rac-1, Mephenesin) by sequential lipase-catalyzed transesterification with vinyl acetate in tetrahydrofuran/triethylamine in the presence of lipase Amano PS is described.
