121985-99-7Relevant academic research and scientific papers
Enzyme Optimization and Process Development for a Scalable Synthesis of (R)-2-Methoxymandelic Acid
Brown, Gareth,Chan, Johann,Dourado, Daniel F. A. R.,Geier, Michael J.,Gray, Darren,Humphreys, Luke D.,Kannan, Balamurali,Mix, Stefan,Pukin, Aliaksei,Scott, Mark E.,Wang, Xiaotian
, (2021)
The rational protein engineering of wild type BCJ2315 nitrilase and its use in the development of a one-pot, enantioselective, dynamic kinetic resolution for (R)-2-methoxymandelic acid is reported. Through a combination of molecular docking and B-factor a
CO2-Mediated Non-Destructive Cyanide Wastewater Treatment
Juhl, Martin,Lee, Ji-Woong,Petersen, Allan R.,Petrovic, Aleksa
supporting information, p. 5003 - 5007 (2021/09/30)
The facile removal of cyanide anions from cyanide-containing water was achieved using CO2 in conjunction with aldehydes which can be recycled from the process. The conversion of the cyanide ion into an insoluble cyanohydrin in water allowed the removal of cyanide and could be used as a method for treating cyanide contaminated wastewater and for recovering cyanide or cyanohydrins for further applications.
CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions**
Juhl, Martin,Petersen, Allan R.,Lee, Ji-Woong
supporting information, p. 228 - 232 (2020/11/30)
Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani–Fischer synthesis under neutral conditions. This protocol offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.
PROCESSES FOR PREPARING ACC INHIBITORS AND SOLID FORMS THEREOF
-
Paragraph 0415, (2018/09/20)
The present disclosure provides solid forms, including a salt or co-crystal, of Compound I which exhibits Acetyl-CoA carboxylase ("ACC") inhibitory activity and may be useful in treating ACC mediated diseases. Also provided herein are processes or steps f
Preparation method of alpha-hydroxypyridine by acetone cyanohydrin
-
Paragraph 0061, (2018/04/01)
The invention relates to a preparation method of alpha-hydroxypyridine by acetone cyanohydrin, and relates to a preparation method of alpha-hydroxypyridine. The method solves the problems that the existing preparation method of the alpha-hydroxypyridine is low in yield, big in catalyst toxicity, high in price, complex in preparation method, and long in reaction time. The method includes steps of firstly, immersing cation exchange resin in 20% by weight of organic amine methanol solution; filtering, washing and drying the solution to obtain catalyst; secondly, dissolving acetone cyanohydrin and aromatic aldehyde in the methanol, and adding catalyst to react and obtain the alpha-hydroxypyridine; filtering the catalyst, depressurizing and evaporating methanol and acetone; extracting and separating the methanol and acetone; after drying, rotationally evaporating and removing ethyl acetate to obtain the alpha-hydroxypyridine. The method applies the simple and easily-prepared catalyst, and the reaction can be completed under room temperature condition; the reaction yield is up to over 95%. The operation method is simple and easy to practice, and the catalyst can be repeatedly used and is more applicable to the industrial production. The preparation method is applied to prepare alpha-hydroxypyridine.
Hydroxynitrile Lyase Isozymes from Prunus communis: Identification, Characterization and Synthetic Applications
Zheng, Yu-Cong,Xu, Jian-He,Wang, Hui,Lin, Guo-Qiang,Hong, Ran,Yu, Hui-Lei
, p. 1185 - 1193 (2017/04/13)
Biocatalysts originating from Badamu (Prunus communis) have been applied to catalyze the asymmetric synthesis of (R)-4-methylsulfanylmandelonitrile, a key building block of thiamphenicol and florfenicol. Here, four hydroxynitrile lyase (HNL) isozymes from Badamu were cloned and heterologously expressed in Pichia pastoris. The biochemical properties and catalytic performances of these isozymes were comprehensively explored to evaluate their efficiency and selectivity in asymmetric synthesis. Among then, PcHNL5 was identified with outstanding activity and enantioselectivity in asymmetric hydrocyanation. Under the optimized mild biphasic reaction conditions, seventeen prochiral aromatic aldehydes were converted to valuable chiral cyanohydrins with good yields (up to 94%) and excellent optical purities (up to >99.9% ee), which provide a facile access to numerous chiral amino alcohols, hypoglycemic agents, angiotension converting enzyme (ACE) inhibitors and β-blockers. This work therefore underlines the importance of discovering the most potent biocatalyst among a group of isozymes for converting unnatural substrates into value-added products. (Figure presented.).
A magnetic nanoparticle catalyzed eco-friendly synthesis of cyanohydrins in a deep eutectic solvent
Azizi, Najmedin,Rahimi, Zahra,Alipour, Masoumeh
, p. 61191 - 61198 (2015/07/28)
Magnetic Fe3O4 nanoparticles in deep eutectic solvents (DESs) have been regard as excellent catalysts for highly efficient cyanosilylation of various aldehydes and epoxides using trimethylsilyl cyanide TMSCN in high yields with excellent selectivity. Fe3O4 nanoparticles were synthesized and applied as a catalyst for the preparation of a wide variety of cyanohydrins (α-hydroxy nitriles and β-hydroxy nitriles) in readily available urea-choline chloride deep eutectic solvent DES as the most promising environmentally benign and cost-effective green solvent. Magnetic DES operates at very mild reaction conditions and can be easily recycled without significant loss of its catalytic activity.
Enantioselective cyanosilylation of aldehydes catalyzed by novel camphor derived Schiff bases-titanium(IV) complexes
B?ocka, Ewelina,Bosiak, Mariusz J.,We?niak, Miros?aw,Ludwiczak, Agnieszka,Wojtczak, Andrzej
, p. 554 - 562 (2014/05/06)
Five tridentate Schiff bases have been prepared from (1R,2S,3R,4S)-3-amino- 1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol and salicylaldehydes. X-ray structure investigation revealed differences in their molecular conformation, and their titanium(IV) complexes
Relationships between the racemic structures of substituted mandelic acids containing 8- and 10-membered hydrogen bonded dimer rings
Coles,Ellis,Leung,Sarson,Threlfall,Tizzard
, p. 10816 - 10823 (2015/02/19)
The structures of 27 monosubstituted mandelic acids, including several of their polymorphs, plus unsubstituted mandelic acid itself (two polymorphs) are investigated for structural similarity. The results, presented pictorially as a structural relationship plot, show that rather more structures are built up from the carboxyl-chain hydroxyl hydrogen bonded dimer than from the conventional carboxylic acid dimer. The results show how all the structures are related and, based on the two types of dimer, the degree of similarity that they possess. Some structures with Z′ > 1 contain both sorts of dimers and there are many examples of isostructural sets within the structures so far determined. We also present an example where analysing similarity in related families of structures highlights a structure that should be present and which has indeed then proceeded to be synthesised and determined.
NaCN/DOWEX(R)50WX4: A convenient system for synthesis of cyanohydrins from aldehydes
Sofighaderi, Sargol,Setamdideh, Davood
, p. 1135 - 1137 (2014/03/21)
A variety of cyanohydrins were prepared from Aldehydes with sodium cyanide and DOWEX(R)50WX4 in a convenient procedure.
