3689-55-2

Usage

Uses

Used in Pharmaceutical Synthesis:
(R,R)-(±)-2-amino-1-(p-nitrophenyl)propane-1,3-diol is used as a chiral building block for the production of antibiotics and other drugs. Its unique structure enables the creation of complex molecules with specific properties, contributing to the development of novel therapeutic agents.
Used in Chromatography:
In the field of analytical chemistry, (R,R)-(±)-2-amino-1-(p-nitrophenyl)propane-1,3-diol serves as a chiral resolving agent in chromatography. This application aids in the separation and identification of enantiomers, which is crucial for understanding the different biological activities and potential side effects of chiral drugs.
Used in Asymmetric Catalysis:
(R,R)-(±)-2-amino-1-(p-nitrophenyl)propane-1,3-diol is also utilized as a building block in the synthesis of chiral ligands for asymmetric catalysis. These ligands are essential in enhancing the selectivity and efficiency of chemical reactions, leading to the production of enantiomerically pure compounds with desired properties.
Used in High-Performance Liquid Chromatography (HPLC):
In the development of chiral stationary phases for HPLC, (R,R)-(±)-2-amino-1-(p-nitrophenyl)propane-1,3-diol is employed to create advanced separation techniques. These techniques are vital for the analysis and purification of chiral compounds, which are prevalent in the pharmaceutical, agrochemical, and fragrance industries.
Used in the Chemical Industry:
(R,R)-(±)-2-amino-1-(p-nitrophenyl)propane-1,3-diol is used as a key intermediate in the synthesis of various organic compounds. Its versatility and reactivity make it a valuable asset in the development of new materials and chemicals with specific applications in different industries.

InChI:InChI=1/C9H12N2O4/c10-8(5-12)9(13)6-1-3-7(4-2-6)11(14)15/h1-4,8-9,12-13H,5,10H2

Upstream product

• 909268-32-2 (1S,2S)-2-acetamido-1-phenylpropane-1,3-diyl diacetate 
• 133269-80-4 (-)-(4R,5R)-1-(4'-nitrophenyl)-1-aza-3,7-dioxabicyclo<3.3.0>octane 
• 51259-82-6 (1R,2R)-1,3-diacetoxy-2-acetylamino-1-(4-nitro-phenyl)-propane 
• 24393-61-1 ethyl (E)-3-(4-nitrophenyl)-2-propenoate 
• 636-98-6 p-nitrobenzene iodide 
• 56-75-7 2-(2,2-dichloroacetylamino)-1-(4-nitrophenyl)propane-1,3-diol 
• 3123-13-5 N-[1-hydroxymethyl-2-(4-nitro-phenyl)-2-oxo-ethyl]-acetamide 
• 100254-93-1 N-[(1RS,2RS)1-hydroxymethyl-2-methoxy-2-(4-nitro-phenyl)-ethyl]-acetamide 
• 108943-99-3 N-(1-acetoxy-3-oxo-3-phenylpropyl)acetamide 
• 104398-16-5 (2RS,3RS)-2-amino-3-methoxy-3-phenyl-propan-1-ol 
• 86022-41-5 (2S,3R)-2-amino-3-hydroxy-3-(4-nitro-phenyl)-propionic acid methyl ester 
• 555-16-8 4-nitrobenzaldehdye 
• 1424360-99-5 (1S,2R,5S,8R,1'R)-5-(1'-hydroxy-p-nitrobenzyl)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one 
• 338-69-2 D-Alanine 

Downstream Products

• 255911-54-7 (1S,2S)-1-(4-nitro-phenyl)-2-[2]pyridylmethylenamino-propane-1,3-diol 
• 1081518-13-9 (1S,2S)-2-benzoylamino-1-(4-nitro-phenyl)-propane-1,3-diol 
• 94622-15-8 N-[(1S,2S)-2-hydroxy-1-hydroxymethyl-2-(4-nitro-phenyl)-ethyl]-phthalamic acid 
• 134-90-7 L-threo-chloramphenicol 
• 10172-89-1 (R)-N-acetylphenylalanin 
• 2018-61-3 (S)-2-acetylamino-3-phenylpropanoic acid 
• 72-19-5 L-threonine 
• 50961-70-1 (1S,2S)-2-amino-1-(4-dimethylamino-phenyl)-propane-1,3-diol 
• 50731-41-4 (1R,2R)-2-amino-1-(4-dimethylamino-phenyl)-propane-1,3-diol 
• 19934-66-8 threo-(1S,2S)-2-acetamino-1-(4-nitrophenyl)-1,3-propanediol 
• 102656-45-1 (1S,2S)-(+)-2-N,N-dibenzylamino-1-(4-nitrophenyl)-1,3-propanediol 
• 109162-23-4 (1S,2S)-1,3-diacetoxy-2-amino-1-(4-nitro-phenyl)-propane; hydrochloride 
• 94000-33-6 [(5S)-5r-hydroxymethyl-6t-(4-nitro-phenyl)-2-oxo-morpholin-3-ylidene]-acetic acid ethyl ester 
• 139925-00-1 2-[(4S,5S)-4-Hydroxymethyl-5-(4-nitro-phenyl)-oxazolidin-2-ylidene]-malononitrile 

Relevant academic research and scientific papers

Binding and action of triphenylphosphonium analog of chloramphenicol upon the bacterial ribosome

Chloramphenicol (CHL) is a ribosome-targeting antibiotic that binds to the peptidyl transferase center (PTC) of the bacterial ribosome and inhibits peptide bond formation. As an approach for modifying and potentially improving the properties of this inhib

Triphenilphosphonium analogs of chloramphenicol as dual-acting antimicrobial and antiproliferating agents

In the current work, in continuation of our recent research, we synthesized and studied new chimeric compounds, including the ribosome-targeting antibiotic chloramphenicol (CHL) and the membrane-penetrating cation triphenylphosphonium (TPP), which are lin

One-Pot Asymmetric Synthesis of an Aminodiol Intermediate of Florfenicol Using Engineered Transketolase and Transaminase

Florfenicol is the 3′-fluoro derivative of thiamphenicol and has been widely used in veterinary medicine for its high antibacterial activity and safety. However, the development of simplified and environmentally friendly catalytic methods for the stereoselective production of florfenicol is a key challenge. Herein, we established a highly stereoselective enzymatic one-pot reaction for the synthesis of an aminodiol intermediate of florfenicol bearing two stereocenters from industrial raw material 4-(methylsulfonyl) benzaldehyde by coupling transketolase (TK) and ω-transaminase (TA). The enantioselectivity of TK from E. coli was converted from (S) (93% ee) to (R) (95% ee), and we also inverted the enantiopreference (E(S) = 9 to E(R) = 12) and ketone/aldehyde substrate selectivity of TA ATA117 via structure-guided enzyme engineering. Docking calculations and molecular dynamics simulations of the wild-type and mutant enzymes unveiled the molecular basis for enzymatic stereocontrol. Using the engineered TK and TA, (1R,2R)-p-methylsulfonyl phenylserinol was biosynthesized with good yield (76%) and high stereoselectivity (96% de and >99% ee). Our work established an enzymatic synthetic route to (1R,2R)-p-methylsulfonyl phenylserinol, facilitating the development of a chemoenzymatic method for producing florfenicol.

ENGINEERED POLYPEPTIDES AND THEIR APPLICATIONS IN SYNTHESIS OF BETA-HYDROXY-ALPHA-AMINO ACIDS

Provided are engineered polypeptides that are useful for the asymmetric synthesis of β-hydroxy-α-amino acids under industrial-relevant conditions. The engineered polypeptides disclosed are developed through directed evolution based on the ability of catalytic synthesis of (2S, 3R) -2-amino-3-hydroxy-3- (4-nitrophenyl) propanoic acid. Also provided are polynucleotides encoding the engineered polypeptides, host cells capable of expressing engineered polypeptides, and methods of producing β-hydroxy-α-amino acids using engineered polypeptides. Compared to other processes of preparation, the use of the engineered polypeptides for the preparation of β-hydroxy-α-amino acids results in high purity of the desired stereoisomers, mild reaction conditions, low pollution and low energy consumption. It has good industrial application prospects.

Stereocontrolled synthesis of syn-β-hydroxy-α-amino acids by direct aldolization of pseudoephenamine glycinamide

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

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

Experimental and DEE study of the conversion of ephedrine derivatives into oxazolidinones. Double SN2 mechanism against SN1 mechanism

Sulfonation of the N-Boc derivatives of 1,2-aminoalcohols, such as ephedrine, pseudoephedrine, norephedrine, norpseudoephedrine, thiomicamine, and chloramphenicol yields a mixture of the corresponding oxazolidinones with inversion (erythro derivatives) and!or retention of configuration (threo derivatives)at C5. We suggest a competition between two mechanisms: an intramolecular SN2 process initiated by attack of the carbonyl oxygen of the Boc group to the benzylic carbon and the other one through a double SN2 process. In the erythro derivatives the first mechanism is predominant, while in the threo derivatives both mechanisms have similar energy. This hypothesis is supported by theoretical calculations and additional experimental assays.

Straightforward access to protected syn α-amino-β-hydroxy acid derivatives

(Chemical Equation Presented) Titanium stability: syn α-Amino-β- hydroxy acid derivatives were prepared in excellent diastereoselectivities by an aldol reaction with chiral N-(azidoacetyl)thiazolidin-2-thione derivatives (see scheme; NMP = N-methylpyrrolidinone). Titanium enolates of these derivatives are stable and provide a new and efficient method to access chiral amino acids.

Method of Preparing Clopidogrel and Intermediates Used Therein

Optically pure clopidogrel can be prepared in a high yield by optically resolving a racemic form of the compound of formula (II) using an optically active amine to form the optically active form of the compound of formula (III) or its acid-addition salt; and methylating the compound of formula (III) or its acid-addition salt.

A short asymmetric total synthesis of chloramphenicol using a selectively protected 1,2-diol

A general route for the synthesis of chloramphenicol, thiamphenicol and fluoramphenicol is described. Chloramphenicol has been synthesized in 45% overall yield.