15318-45-3Relevant articles and documents
Regioselective preparation of thiamphenicol esters through lipase-catalyzed processes
Da Silva, Marcos R.,Montenegro, Tasso G.C.,De Mattos, Marcos C.,De Oliveira, Maria Da Conceic?a?o F.,De Lemos, Telma L.G.,De Gonzalo, Gonzalo,Lavandera, Iva?n,Gotor-Ferna?ndez, Vicente,Gotor, Vicente
, p. 987 - 994 (2014)
The lipase-catalyzed synthesis of thiamphenicol derivatives has been studied through complementary acylation and hydrolytic approaches, finding Candida antarctica lipase B as the most efficient biocatalyst for the selective modification of both thiampheni
An Efficient Stereoselective Total Synthesis of All Stereoisomers of the Antibiotic Thiamphenicol through Ruthenium-Catalyzed Asymmetric Reduction by Dynamic Kinetic Resolution
Perez, Marc,Echeverria, Pierre-Georges,Martinez-Arripe, Elsa,Ez Zoubir, Mehdi,Touati, Ridha,Zhang, Zhaoguo,Genet, Jean-Pierre,Phansavath, Phannarath,Ayad, Tahar,Ratovelomanana-Vidal, Virginie
, p. 5949 - 5958 (2015)
Thiamphenicol is a widely used antibiotic that exhibits activity against numerous Gram-positive and Gram-negative pathogens. Here, we describe the expedient synthesis of its four stereoisomers through a dynamic kinetic resolution that follows a ruthenium-catalyzed asymmetric hydrogenation or a hydrogen transfer reaction as the key step.
Method for continuously preparing thiamphenicol by using micro-reaction system
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Paragraph 0021-0043, (2021/08/14)
The invention belongs to the technical field of pharmaceutical engineering, and particularly relates to a method for continuously preparing thiamphenicol by using a micro-reaction system. A micro-reaction system used in the method comprises a micro-mixer, a micro-channel reactor and a back pressure device, and during preparation, a solution of raw materials (1R,2R)-2-amino-1-(4-(methylsulfonyl)phenyl)propane-1,3-diol and an alkaline solution of methyl dichloroacetate are simultaneously injected into the micro-reactor by a pump respectively for condensation reaction, and concentrating, recrystallizing, filtering, washing and drying are conducted on the reaction product to obtain a thiamphenicol product. According to the method provided by the invention, the reaction time is only several minutes, the yield of the product thiamphenicol is greater than 99%, the purity is greater than 99%, the operation is convenient, continuous and controllable, the amplification effect is avoided, the efficiency of the technological process is high, and the method has a very good industrial application prospect.
Catalytic Syn-Selective Nitroaldol Approach to Amphenicol Antibiotics: Evolution of a Unified Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, (+)-Thiamphenicol, and (+)-Florfenicol
Chen, Fener,Cheng, Dang,Huang, Huashan,Jiang, Meifen,Liu, Minjie,Qu, Hongmin,Xia, Yingqi,Xiong, Tong,Zhang, Yan
, p. 11557 - 11570 (2021/09/02)
A unified strategy for an efficient and high diastereo- and enantioselective synthesis of (-)-chloramphenicol, (-)-azidamphenicol, (+)-thiamphenicol, and (+)-florfenicol based on a key catalytic syn-selective Henry reaction is reported. The stereochemistry of the ligand-enabled copper(II)-catalyzed aryl aldehyde Henry reaction of nitroethanol was first explored to forge a challenging syn-2-amino-1,3-diol structure unit with vicinal stereocenters with excellent stereocontrol. Multistep continuous flow manipulations were carried out to achieve the efficient asymmetric synthesis of this family of amphenicol antibiotics.
Unified Strategy to Amphenicol Antibiotics: Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, and (+)-Thiamphenicol and Its (+)-3-Floride
Liu, Jinxin,Li, Yaling,Ke, Miaolin,Liu, Minjie,Zhan, Pingping,Xiao, You-Cai,Chen, Fener
, p. 15360 - 15367 (2020/11/30)
The asymmetric synthesis of (-)-chloramphenicol, (-)-azidamphenicol, and (+)-thiamphenicol and its (+)-3-floride, (+)-florfenicol, is reported. This approach toward the amphenicol antibiotic family features two key steps: (1) a cinchona alkaloid derived urea-catalyzed aldol reaction allows highly enantioselective access to oxazolidinone gem-diesters and (2) a continuous flow diastereoselective decarboxylation of thermally stable oxazolidinone gem-diesters to form the desired trans-oxazolidinone monoesters with two adjacent stereocenters that provide the desired privileged scaffolds of syn-vicinal amino alcohols in the amphenicol family.
Thiamphenicol synthesis method
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Paragraph 0008, (2020/01/25)
The invention discloses a thiamphenicol synthesis method which comprises the following steps: by adopting D-p-methylsulfonylphenyl serine ethyl ester as a starting raw material, performing reduction with potassium borohydride or sodium borohydride, cyclizing the starting raw material with dichloroacetonitrile in an environment that an organic acid is added to adjust a pH value, and performing hydrolysis with hydrochloric acid to obtain thiamphenicol. The method is simple in process operation, easily available in raw material and high in conversion rate, and the cost can be greatly reduced.
Florfenicol intermediate synthesis method
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, (2019/07/04)
The invention belongs to the field of synthesis of pharmaceutical raw materials, and specifically discloses a florfenicol intermediate synthesis method, which comprises: (1) carrying out a reaction ona compound (II) and an acylating reagent in an organic solvent to form a compound (III); (2) carrying out a reaction on the compound (III) and an oxidizing agent in an organic solvent in the presenceof a catalyst to form a compound (IV); (3) carrying out a reaction on the compound (IV) and a fluorinating reagent in an organic solvent to form a compound (V); and (4) carrying out acidolysis on thecompound (V) in an organic solvent, and carrying out deprotection to obtain a compound (I), wherein various groups in the formulas are defined in the specification. According to the present invention, the florfenicol intermediate can be used for preparing florfenicol; and the method has characteristics of novel design, mild conditions and simple operation, and is suitable for industrial production.
Asymmetric Synthesis of Florfenicol by Dynamic Reductive Kinetic Resolution with Ketoreductases
Zou, Jie,Ni, Guowei,Tang, Jiawei,Yu, Jun,Jiang, Luobin,Ju, Dianwen,Zhang, Fuli,Chen, Shaoxin
, p. 5044 - 5053 (2018/10/05)
A chemoenzymatic synthesis of the veterinary antibiotic florfenicol is described. The key step involves the dynamic reductive kinetic resolution (DYRKR) of a keto ester by using a ketoreductase-02 (KRED-02) to afford the two contiguous stereocenters of the (2S,3R)-cis-1,2-amino alcohol intermediate in >99 % ee and a diastereomeric ratio (dr) of 99 %. This green biocatalysis is environmental friendly with high enantioselectivity and product yields. Two methods for the nucleophilic fluorination step involved the use of aziridines and cyclic sulfates to safely prepare fluoroamines with high regioselectivity. Additional studies have indicated that KRED-02 can also be used to afford chiral alcohol (S)-21 in good yields with high enantioselectivity. This study shows that the integration of biocatalysis into organic synthesis can be useful and provide industrial opportunities for applications of florfenicol.
Stereocontrolled synthesis of syn-β-hydroxy-α-amino acids by direct aldolization of pseudoephenamine glycinamide
Seiple, Ian B.,Mercer, Jaron A. M.,Sussman, Robin J.,Zhang, Ziyang,Myers, Andrew G.
supporting information, p. 4642 - 4647 (2014/05/20)
β-Hydroxy-α-amino acids figure prominently as chiral building blocks in chemical synthesis and serve as precursors to numerous important medicines. Reported herein is a method for the synthesis of β-hydroxy- α-amino acid derivatives by aldolization of pseudoephenamine glycinamide, which can be prepared from pseudoephenamine in a one-flask protocol. Enolization of (R,R)- or (S,S)-pseudoephenamine glycinamide with lithium hexamethyldisilazide in the presence of LiCl followed by addition of an aldehyde or ketone substrate affords aldol addition products that are stereochemically homologous with L- or D-threonine, respectively. These products, which are typically solids, can be obtained in stereoisomerically pure form in yields of 55-98 %, and are readily transformed into β-hydroxy-α-amino acids by mild hydrolysis or into 2-amino-1,3-diols by reduction with sodium borohydride. This new chemistry greatly facilitates the construction of novel antibiotics of several different classes. On aldol: Enolization of (R,R)- or (S,S)-pseudoephenamine glycinamide with lithium hexamethyldisilazide (LiHMDS) in the presence of LiCl followed by addition of either an aldehyde or ketone substrate affords aldol addition products which are stereochemically homologous with L- or D-threonine, respectively. These products can be obtained in stereoisomerically pure form in yields of 55-98 %, and are readily transformed into β-hydroxy-α-amino acids by mild hydrolysis or into 2-amino-1,3-diols by reduction.
Stereoselective synthesis of (-)-chloramphenicol, (+)-thiamphenicol and (+)-sphinganine via chiral tricyclic iminolactone
Li, Qiong,Zhang, Hongbo,Li, Chenguang,Xu, Pengfei
supporting information, p. 149 - 153 (2013/08/24)
The stereoselective syntheses of (-)-chloramphenicol, (+)-thiamphenicol and (+)-sphinganine are described. The two continuous chiral centers within three target molecules were constructed through aldol reaction of chiral tricyclic iminolactone and aldehyde. Concise and efficient syntheses of (-)-chloramphenicol, (+)-thiamphenicol and (+)-sphinganine have been accomplished in practical four or three steps. The synthetic route featured in an aldol reaction between iminolactone 1a and 1b with aldehyde, which introduced the two continuous chiral centers within three target molecules. Copyright
