333381-39-8Relevant articles and documents
Regioselective acetylation of carbohydrates and diols catalyzed by tetramethyl-ammonium hydroxide in water
Lu, Yuchao,Wei, Peng,Pei, Yuxin,Xu, Hengfu,Xin, Xiaoting,Pei, Zhichao
, p. 4510 - 4514 (2014/12/10)
A novel method for an efficient regioselective acetylation of carbohydrates and diols in aqueous solution is described. Treatment of substrates with 1-acetylimidazole, and tetramethyl-ammonium hydroxide (TMAH) in water under mild conditions gave highly regioselective acetylation for primary hydroxyl groups. This discovery provides an eco-friendly way for selective acetylation of non-protected glycosides and diols in water, avoiding the use of toxic organic solvents and the necessity of pre-protection of secondary hydroxyl groups. This journal is
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.