957509-27-2Relevant articles and documents
Green synthesis of (R)-3-TBDMSO glutaric acid methyl monoester using Novozym 435 in non-aqueous media
Wang, Hongjiang,Li, Zebiao,Yu, Xiaoxia,Chen, Ruidong,Chen, Xiulai,Liu, Liming
, p. 75160 - 75166 (2015/09/21)
An efficient biocatalytic synthesis of (R)-3-TBDMSO glutaric acid methyl monoester (R-J6), an important intermediate in the synthesis of rosuvastatin, has been developed using a green catalytic route in the presence of lipase, conducted under mild conditions without additional chiral reagents. Enzyme screening indicated Novozym 435 to be the most efficient biocatalyst for R-J6 synthesis. Methanol, which was the most effective alcohol for synthesis of R-monoester, was identified as the best acyl acceptor by molecular docking. The optimal conditions for synthesis of R-J6 were as follows: 50 g L-1 catalyst, 3 sp;:sp;1 molar ratio of methanol sp;:sp;substrate, 200 g L-1 substrate, iso-octane as solvent, orbital shaking at 200 rpm, and an incubation time of 24 h at 35°C. The key factor affecting the yield of R-J6 was the molar ratio of methanol to substrate found by an orthogonal array experimental design. Consequently, the desired product, R-J6, was afforded with a titer of 117.2 g L-1, a yield of 58.6%, and productivity of 4.88 g L-1 h-1. This green method holds promise for the preparation of kilogram quantities of (R)-3-substituted glutaric acid monoesters.
Enzymatic synthesis of (S)-glutaric acid monoesters aided by molecular docking
Wang, Bo,Liu, Ji,Tang, Xiaoling,Cheng, Cheng,Gu, Jiali,Dai, Liyan,Yu, Hongwei
supporting information; experimental part, p. 309 - 312 (2010/03/04)
An efficient enzymatic method for the synthesis of (S)-3-substituted glutaric acid monoesters which was aided by molecular docking has been described. The reaction was proceeded under mild conditions, and the desired products were afforded with up to 98%
