《One-pot enzymatic synthesis of enantiopure 1,3-oxathiolanes using Trichosporon laibachii lipase and the kinetic model》 was written by Zhang, Yuanyuan; Sun, Yangjian; Tang, Hui; Zhao, Qiuxiang; Ren, Wenjie; Lv, Kuiying; Yang, Fengke; Wang, Fanye; Liu, Junhong. SDS of cas: 60656-87-3 And the article was included in Organic Process Research & Development in 2020. The article conveys some information:
The dynamic covalent kinetic resolution protocol was efficiently used for the synthesis of the enantiopure ((R)-5-acetoxy-1,3-oxathiolan-2-yl)ethyl benzoate (PR) from substrates 2-(phenylmethoxy)acetaldehyde (A), 1,4-dithiane-2,5-diol (B), and Ph acetate (D) by a one-pot process with 99.6% conversion, 97.3% yield, and 96.5% ee through the combination of reversible hemithioacetal transformation and enantiomer-selective lactonization catalyzed by immobilized lipase from Trichosporon laibachii. A proposed kinetic model consisting of transformation and lactonization was developed herein for the first time, fitting the exptl. data very well. It was concluded that (1) the transformation in a chem. fashion may follow a power law. (2) The enzymic lactonization may follow a sequential mechanism with product inhibition. The reaction kinetic data reveal that phenol (P1) would have strong product inhibition, while noncompetitive inhibition, product inhibition of PR, and substrate inhibition were not recognized. The model suggests that there is a common limitation of both enzyme and chem. in the chemo-enzymic system, and thus the amount of lipase was increased to accelerate the enzymic lactonization and to reduce the limitation caused by the enzymic reaction, resulting in the increase of the yield of PR significantly. The exptl. results demonstrate that both the internal and external mass diffusion resistance could be negligible, and thus the kinetic model developed is the inherent kinetic one. In the part of experimental materials, we found many familiar compounds, such as 2-(Benzyloxy)acetaldehyde(cas: 60656-87-3SDS of cas: 60656-87-3)
2-(Benzyloxy)acetaldehyde(cas: 60656-87-3) is a non-natural aldehyde. It undergoes enantioselective Mukaiyama aldol reaction with silylketene acetal nucleophiles in the presence of C2-symmetric bis(oxazolinyl)pyridine Cu(II) complex (catalyst).SDS of cas: 60656-87-3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem