147220-29-9Relevant articles and documents
A biocatalytic approach for regioselective monoacetylation of 3-aryloxy-1,2-propanediols by porcine pancreatic lipase
Meena, Vachan Singh,Banerjee
experimental part, p. 951 - 953 (2012/08/29)
Among the various lipases screened for the regioselective monoacetylation of 3-aryloxy-1,2-propanediols, porcine pancreatic lipase was found to afford a higher yield. The selectivity for the monoacetylation process was maximized by using different organic solvents and diisopropyl ether gave the highest conversion to monoacetylated product (ca. 98%). The optimized reaction afforded excellent yields of the monoacetylated product with regioselectivity at the terminal hydroxyl group in the presence of various aryl substituents in the starting material. Springer-Verlag 2011.
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.
