1607830-33-0Relevant 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.
Synthesis of GABOB and GABOB-based chiral units possessing distinct protecting groups
Ivsic, Trpimir,Dokli, Irena,Rimac, Ana,Hamersak, Zdenko
, p. 631 - 638 (2014/02/14)
In addition to the varied biological activity of GABOB (4-amino-3- hydroxybutanoic acid), the structure of its protected derivatives makes them interesting chiral intermediates for the synthesis of more complex compounds. A stereoselective route to GABOB derivatives with three different protecting groups is presented, using anhydride desymmetrization as a chirality-inducing step. Selective removal of the protecting groups gave compounds with a free carboxylic acid or hydroxy group. Removal of all of the protecting groups allowed GABOB to be isolated in good yield and with excellent ee. A stereoselective route to GABOB (4-amino-3-hydroxybutanoic acid) derivatives with three different protecting groups is presented. Selective deprotection produced diprotected chiral building blocks with a free carboxylic acid or hydroxy group. Removal of all the protecting groups allowed GABOB to be isolated. Copyright
