37577-28-9

Usage

InChI:InChI=1/C9H13NO.ClH/c1-7(10)9(11)8-5-3-2-4-6-8;/h2-7,9,11H,10H2,1H3;1H/t7-,9-;/m0./s1

Upstream product

• 14838-15-4 u-2-amino-1-phenylpropan-1-ol 
• 917-64-6 methyl magnesium iodide 
• 131350-12-4 (S)-2-phenyl-2-(trimethylsiloxy)acetonitrile 
• 97-96-1 2-Ethylbutyraldehyde 
• 93714-15-9 (4R,5S)-2,2,4-Trimethyl-5-phenyl-oxazolidine 
• 154-41-6 erythro-1-phenyl-1-hydroxy-2-propylammonium chloride 
• 28549-12-4 (S)-mandelonitrile 
• 90-63-1 (RS)-1-hydroxy-1-phenylpropan-2-one 
• 862789-34-2 (1S,2R)-2-nitro-1-phenylpropan-1-ol 
• 100-52-7 benzaldehyde 
• 26251-08-1 2-nitro-1-phenylpropan-1-ol 
• 67755-90-2 Ethoxy-1-ethoxy-(phenyl)-acetonitrile 
• 131472-76-9 2-(Benzhydrylidene-amino)-1-phenyl-propan-1-ol 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 

Downstream Products

• 591733-72-1 (4R,5S)-(+)-4-methyl-5-phenyloxazolidin 
• 56571-91-6 (1S,2R)-(+)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol 
• 133576-75-7 (+)-(1S,2R)-1-Phenyl-2-(1-piperidinyl)propan-1-ol 
• 144490-24-4 2,2-Dichloro-N-((1R,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-acetamide 
• 20330-18-1 N⁶-<(1S,2R)-1-hydroxy-1-phenyl-2-propyl>adenosine 
• 114389-70-7 (1S,2R)-(-)-2-(N,N-di-n-butylamino)-1-phenylpropan-1-ol 
• 127566-16-9 (1S,2R)-(-)-2-(N,N-di-n-heptylamino)-1-phenylpropan-1-ol 
• 127566-17-0 (1S,2R)-(-)-2-(N,N-di-n-octylamino)-1-phenylpropan-1-ol 
• 128812-08-8 (1S,2R)-(+)-2-(N,N-diallylamino)-1-phenylpropan-1-ol 
• 134566-98-6 (1S,2R)-(+)-2-(N,N-diisobutylamino)-1-phenylpropan-1-ol 
• 132537-80-5 -α-<1-<(1-phenyl-6-chloro-1H-pyrazolo<3,4-d>pyrimidin-4-yl)amino>ethyl>benzenemethanol 
• 117409-03-7 (4R,5S)-(-)-4-Methyl-5-phenyl-2-(2-pyridinyl)-2-oxazolin 
• 127641-24-1 (1S,2R)-(-)-2-(N,N-di-n-propylamino)-1-phenylpropan-1-ol 
• 136846-24-7 (4R,5S)-4-methyl-5-phenyl-2-oxazoline 

Relevant academic research and scientific papers

Template polymerization of columnar architectures based on the salts of a carboxylic acid and 2-amino alcohols: Application to the molecular recognition of 2-amino alcohols

The salts of trialkoxybenzoic acids and 2-amino alcohols showed a columnar liquid crystalline phase; in the case of the salt of a polymerizable acid and norephedrine, the photopolymerization proceeded efficiently in the liquid crystalline state, and the resultant solid adsorbed 2-amino alcohols size, regio-, and enantio-selectively.

High Regio- and Stereoselective Multi-enzymatic Synthesis of All Phenylpropanolamine Stereoisomers from β-Methylstyrene

We present a one-pot cascade for the synthesis of phenylpropanolamines (PPAs) in high optical purities (er and dr up to >99.5 %) and analytical yields (up to 95 %) by using 1-phenylpropane-1,2-diols as key intermediates. This bioamination entails the combination of an alcohol dehydrogenase (ADH), an ω-transaminase (ωTA) and an alanine dehydrogenase to create a redox-neutral network, which harnesses the exquisite and complementary regio- and stereo-selectivities of the selected ADHs and ωTAs. The requisite 1-phenylpropane-1,2-diol intermediates were obtained from trans- or cis-β-methylstyrene by combining a styrene monooxygenase with epoxide hydrolases. Furthermore, in selected cases, the envisioned cascade enabled to obtain the structural isomer (1S,2R)-1-amino-1-phenylpropan-2-ol in high optical purity (er and dr >99.5 %). This is the first report on an enzymatic method that enables to obtain all of the four possible PPA stereoisomers in great enantio- and diastereo-selectivity.

Regio- and stereoselective multi-enzymatic aminohydroxylation of β-methylstyrene using dioxygen, ammonia and formate

We report an enzymatic route for the formal regio- and stereoselective aminohydroxylation of β-methylstyrene that consumes only dioxygen, ammonia and formate; carbonate is the by-product. The biocascade entails highly selective epoxidation, hydrolysis and hydrogen-borrowing alcohol amination. Thus, β-methylstyrene was converted into 1R,2R and 1S,2R-phenylpropanolamine in 59-63% isolated yields, and up to >99.5 : 0.5 dr and er.

AMINOGLYCOSIDE ANTIBIOTICS

Provided herein are aminoglycosides for the treatment of infections, and pharmaceutical compositions, methods, kits, and uses thereof. Also provided are a methods of making aminoglycosides that enables late-stage derivatization of the C6' and C3 " amino groups, thereby allowing facile access to previously inaccessible aminoglycosides.

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.

Stereoselective Catalytic Synthesis of Active Pharmaceutical Ingredients in Homemade 3D-Printed Mesoreactors

3D-printed flow reactors were designed, fabricated from different materials (PLA, HIPS, nylon), and used for a catalytic stereoselective Henry reaction. The use of readily prepared and tunable 3D-printed reactors enabled the rapid screening of devices with different sizes, shapes, and channel dimensions, aimed at the identification of the best-performing reactor setup. The optimized process afforded the products in high yields, moderate diastereoselectivity, and up to 90 % ee. The method was applied to the continuous-flow synthesis of biologically active chiral 1,2-amino alcohols (norephedrine, metaraminol, and methoxamine) through a two-step sequence combining the nitroaldol reaction with a hydrogenation. To highlight potential industrial applications of this method, a multistep continuous synthesis of norephedrine has been realized. The product was isolated without any intermediate purifications or solvent switches.

Efficient 2-step biocatalytic strategies for the synthesis of all nor(pseudo)ephedrine isomers

Chiral 1,2-amino alcohols are important building blocks for chemistry and pharmacy. Here, we developed two different biocatalytic 2-step cascades for the synthesis of all four nor(pseudo)ephedrine (N(P)E) stereoisomers. In the first one, the combination of an (R)-selective thiamine diphosphate (ThDP)-dependent carboligase with an (S)- or (R)-selective ω-transaminase resulted in the formation of (1R,2S)-NE or (1R,2R)-NPE in excellent optical purities (ee >99% and de >98%). For the synthesis of (1R,2R)-NPE, space-time yields up to ～26 g L-1 d-1 have been achieved. Since a highly (S)-selective carboligase is currently not available for this reaction, another strategy was followed to complement the nor(pseudo)ephedrine platform. Here, the combination of an (S)-selective transaminase with an (S)-selective alcohol dehydrogenase yielded (1S,2S)-NPE with an ee >98% and a de >99%. Although lyophilized whole cells are cheap to prepare and were shown to be appropriate for use as biocatalysts, higher optical purities were observed with purified enzymes. These synthetic enzyme cascade reactions render the N(P)E-products accessible from inexpensive, achiral starting materials in only two reaction steps and without the isolation of the reaction intermediates. This journal is the Partner Organisations 2014.

A Highly anti-selective asymmetric henry reaction catalyzed by a chiral copper complex: Applications to the syntheses of (+)-spisulosine and a pyrroloisoquinoline derivative

A highly anti-selective asymmetric Henry reaction has been developed, affording synthetically versatile β-nitroalcohols in a predominately anti-selective manner (mostly above 15:1) and excellent ee values (mostly above 95 %). Moreover, the anti-selective Henry reaction was carried out in the presence of water for the first time with up to 99 %-ee. The catalytic mechanism was proposed based on the detection of the intermediates by extractive electrospray ionization mass spectrometry (EESI-MS). Furthermore, the anti adducts have been successfully transformed into the biochemically important (+)-spisulosine and a pyrroloisoquinoline derivative. Copyright

Stereoselective synthesis of norephedrine and norpseudoephedrine by using asymmetric transfer hydrogenation accompanied by dynamic kinetic resolution

Each of the enantiomers of both norephedrine and norpseudoephedrine were stereoselectively prepared from the common, prochiral cyclic sulfamidate imine of racemic 1-hydroxy-1-phenyl-propan-2-one by employing asymmetric transfer hydrogenation (ATH) catalyzed by the well-defined chiral Rh-complexes, (S,S)- or (R,R)-Cp*RhCl(TsDPEN), and HCO2H/Et3N as the hydrogen source. The ATH processes are carried out under mild conditions (rt, 15 min) and are accompanied by dynamic kinetic resolution.

Charge-transfer interactions: An efficient tool for recycling bis(oxazoline)-copper complexes in asymmetric henry reactions

An anthracenyl-modified chiral bis(oxazoline) copper complex has been demonstrated to efficiently promote nitroaldol reactions between structurally varying aldehydes and nitromethane or nitroethane. The catalyst was recovered through formation of a charge transfer complex between the chiral ligand and trinitrofluorenone and its subsequent precipitation with pentane. The efficiency of this procedure was proved through several consecutive catalytic cycles that allowed the sturdy formation of the expected product with a high enantioselectivity. The catalyst′s stability was also put to the test in an original multi-substrate procedure. Following the same recovery concept, a new heterogeneous procedure was tested for which trinitrofluorenone was covalently linked to a silica support. Asymmetric heterogeneous catalysis was performed under these conditions as one of the few examples demonstrating the potential catalyst recycling in nitroaldol reactions through reversible, non-covalent interactions. Copyright