22821-77-8Relevant articles and documents
Chiral resolution of racemic p-methylsulfonylphenyl serine ethyl ester with lipases: The mechanism of side reaction and its suppression
Guo, Rui,Fan, Yong-Xian,Chen, Xiao-Long,Shen, Yin-Chu
, p. 157 - 166 (2013)
The d-threo form of p-methylsulfonylphenyl serine ethyl ester (MPSE) is a key intermediate for the synthesis of florfenicol. In this study, chiral resolution of dl-threo-p-MPSE with lipases was investigated. Among a series of lipases, Novzyme 435 was the best to resolve dl-threo-p-MPSE with the conversion rate of 36.83% and ee value of 35.13%. To improve the conversion rate and ee value, a number of byproducts were identified and characterized using reverse-phase HPLC, normal-phase HPLC, 1H NMR, and LC-MS when threo-p-MPSE was hydrolyzed by lipases in organic medium. Mechanisms of generating main byproducts are proposed, and a suppressing method is provided. The results showed that byproduct p-methylsulfonyl benzaldehyde serves as the key intermediate during the whole side reaction process. It was also observed that threo-p-MPSE with a proper hydrolytic velocity served as a driving force to generate p-methylsulfonyl benzaldehyde and accelerated the side reactions. Finally, a feasible approach to suppress side reactions in enzymatic catalysis is offered. The conversion rate and ee value were greatly improved by 69.29 and 46.26%, respectively, using Zn2+ compared to those without Zn 2+.
COMPOSITES, METHODS AND USES THEREOF
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Page/Page column 26, (2021/06/04)
The present invention relates, in general terms, to methods of catalysing a reaction, including the steps of contacting a chemical entity comprising a sulphide moiety with a composite and an oxidant. The composite acts as a heterogeneous catalyst to oxidise the sulphide moiety. The present invention also relates to composites, methods of synthesising the composites and its use as a catalyst thereof.
Regio- A nd chemoselective deprotection of primary acetates by zirconium hydrides
Gavel, Marine,Courant, Thibaut,Joosten, Antoine Yvan Philippe,Lecourt, Thomas
supporting information, p. 1948 - 1952 (2019/04/10)
A combination of DIBAL-H and Cp2ZrCl2 is shown to promote the regioselective cleavage of primary acetates on a broad scope of substrates, ranging from carbohydrates to terpene derivatives, with a high tolerance toward protecting groups and numerous functionalities found in natural products and bioactive compounds. Apart from providing highly valuable building blocks in only two steps from biosourced raw materials, this selective de-O-acetylation should also be strongly helpful to solve selectivity issues in organic synthesis.