297765-46-9

Upstream product

• 6595-30-8 2-azido-1-(4-methylphenyl)ethan-1-one 
• 183540-43-4 (S)-(+)-1-(4-Tolyl)-2-(p-tolylsulfonyloxy)ethanol 
• 104-87-0 4-methyl-benzaldehyde 
• 139016-20-9 (S)-1-(4-methylphenyl)-1,2-ethanediol 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 619-41-0 4-(bromoacetyl)toluene 
• 144924-03-8 2-azido-1-(4-methylphenyl)ethanol 

Downstream Products

• 149403-05-4 (S)-1-(4'-methylphenyl)-2-aminoethanol 
• 924651-48-9 1-[(S)-2-azido-1-(methoxymethoxy)ethyl]-4-methylbenzene 

Relevant academic research and scientific papers

Asymmetric synthesis of 2-azido-1-arylethanols from azido aryl ketone-β-cyclodextrin complexes and sodium borohydride in water

β-Cyclodextrin catalyses for the first time the asymmetric reduction of α-azido aryl ketones to corresponding alcohols of great significance using sodium borohydride in water. The azido group appeared to be the best fit among various groups studied. This

Norepinephrine alkaloids as antiplasmodial agents: Synthesis of syncarpamide and insight into the structure-activity relationships of its analogues as antiplasmodial agents

Syncarpamide 1, a norepinephrine alkaloid isolated from the leaves of Zanthoxylum syncarpum (Rutaceae) exhibited promising antiplasmodial activities against Plasmodium falciparum with reported IC50 values of 2.04 μM (D6 clone), 3.06 μM (W2 clone) and observed by us 3.90 μM (3D7 clone) and 2.56 μM (K1 clone). In continuation of our work on naturally occurring antimalarial compounds, synthesis of syncarpamide 1 and its enantiomer, (R)-2 using Sharpless asymmetric dihydroxylation as a key step has been accomplished. In order to study structure-activity-relationship (SAR) in detail, a library of 55 compounds (3–57), which are analogues/homologues of syncarpamide 1 were synthesized by varying the substituents on the aromatic ring, by changing the stereocentre at the C-7 and/or by varying the acid groups in the ester and/or amide side chain based on the natural product lead molecule and further assayed in vitro against 3D7 and K1 strains of P. falciparum to evaluate their antiplasmodial activities. In order to study the effect of position of functional groups on antiplasmodial activity profile, a regioisomer (S)-58 of syncarpamide 1 was synthesized however, it turned out to be inactive against both the strains. Two compounds, (S)-41 and its enantiomer, (R)-42 having 3,4,5-trimethoxy cinnamoyl groups as side chains showed better antiplasmodial activity with IC50 values of 3.16, 2.28 μM (3D7) and 1.78, 2.07 μM (K1), respectively than the natural product, syncarpamide 1. Three compounds (S)-13, (S)-17, (S)-21 exhibited antiplasmodial activities with IC50 values of 6.39, 6.82, 6.41 μM against 3D7 strain, 4.27, 7.26, 2.71 μM against K1 strain and with CC50 values of 147.72, 153.0, >200 μM respectively. The in vitro antiplasmodial activity data of synthesized library suggests that the electron density and possibility of resonance in both the ester and amide side chains increases the antiplasmodial activity as compared to the parent natural product 1. The natural product syncarpamide 1 and four analogues/homologues out of the synthesized library of 55, (S)-41, (R)-42, (S)-55 and (S)-57 were assayed in vivo assay against chloroquine-resistant P. yoelii (N-67) strain of Plasmodium. However, none of the five molecules, 1, (S)-41, (R)-42, (S)-55 and (S)-57 exhibited any promising in vivo antimalarial activity against P. yoelii (N-67) strain. Compounds 4, 6, 7 and 11 showed high cytotoxicities with CC50 values of 5.87, 5.08, 6.44 and 14.04 μM, respectively. Compound 6 was found to be the most cytotoxic as compared to the standard drug, podophyllotoxin whereas compounds 4 and 7 showed comparable cytotoxicities to podophyllotoxin.

One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.

Synthesis of optically pure 2-azido-1-arylethanols with isolated enzymes and conversion to triazole-containing β-blocker analogues employing click chemistry

(Chemical Equation Presented) Both antipodes of 2-azido-1-arylethanols were synthesized with excellent optical purity via enzymatic reduction of the corresponding α-azidoacetophenone derivatives catalyzed by a recombinant carbonyl reductase from Candida m

A new asymmetric synthetic route to substituted piperidines

An asymmetric synthesis of substituted piperidines has been described. β-Cyclodextrin- or oxazaborolidine-catalyzed asymmetric reduction of α-azido aryl ketones to the corresponding alcohols has been employed as the key step along with ring closing metathesis and selective dihydroxylation.

Pd-catalyzed oxidative kinetic resolution of 2-azido-1-arylethanols

(-)-Sparteine/ Pd (II) complex in combination with oxygen as a stoichiometric oxidant, catalyses the oxidative kinetic resolution of β-azido alcohols to afford the corresponding chiral 2-azido-1-arylethanols.

Application of optically active 1,2-diol monotosylates for synthesis of β-azido and β-amino alcohols with very high enantiomeric purity. Synthesis of enantiopure (R)-octopamine, (R)-tembamide and (R)-aegeline

A very convenient and highly efficient synthesis of near enantiopure β-azido and β-amino alcohols including biologically active substances such as (R)-octopamine, (R)-tembamide and (R)-aegeline from optically active 1,2-diol monotosylates is reported.

Efficient synthesis of optically active 2-azido-1-arylethanols via oxazaboronlidine - Catalysed asymmetric borane reduction

A simple, efficient, stereo- and regio-selective method for the synthesis of optically active 2-azido-1-phenylethanols by asymmetric reduction of 2-azidoacetophenones with in situ generated, oxazaborolidine- borane complexes in THF, is described. This new method appears to be an alternative to the classical methods previously reported.