91420-74-5

Upstream product

• 27720-03-2 S-2-(Dimethylamino)-3-phenyl-1-propanol 
• 70987-78-9 (S)-Glycidyl tosylate 
• 591-51-5 phenyllithium 
• 155498-78-5 Toluene-4-sulfonic acid (R)-2-hydroxy-3-phenyl-propyl ester 
• 300-57-2 allylbenzene 
• 4436-24-2 1,2-epoxy-3-phenylpropane 
• 937-38-2 1-chloro-3-phenylpropan-2-one 
• 67-56-1 methanol 
• 91465-27-9 N,N-dimethyl-L-phenylalanine ethyl ester 
• 3081-24-1 H-Phe-OEt 
• 114395-16-3 [(2S,3S)-3-phenyloxiran-2-yl]methyl 4-methylbenzenesulfonate 
• 121958-41-6 [(2R,3R)-3-phenyloxiran-2-yl]methyl 4-methylbenzenesulfonate 
• 17131-14-5 (S)-(-)-3-phenyl-1,2-propanediol 
• 104-53-0 3-phenyl-propionaldehyde 

Downstream Products

• 1028809-59-7 (S)-1-[(3S,6S)-6-benzhydrylpiperidin-3-ylamino]-3-phenylpropan-2-ol 
• 1222139-25-4 1-(3-bromophenyl)-3-phenyl-2(S)-propanol 
• 1378381-35-1 1,12-dibenzyl-(2R,11R)-dodecane-2.11-diol 
• 1378382-20-7 (R)-1-phenyltridec-12-en-2-ol 
• 17131-14-5 (S)-(-)-3-phenyl-1,2-propanediol 
• 220589-10-6 (S)-2-hydroxy-3-phenylpropanal 
• 125043-43-8 C₁₆H₁₇N 
• 1204181-89-4 1-phenyl-5-trimethylsilanyl-pent-4-yn-2-(R)-ol 
• 1222135-38-7 3-[(2(S)-azetidinyl)methoxy]-5-[3-(2(S)-methoxy-3-phenylpropyl)phenyl]pyridine 
• 1222139-38-9 3-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-5-[3-(2(S)-methoxy-3-phenylpropyl)phenyl]pyridine 
• 1222139-36-7 1-bromo-3-(2 (S)-methoxy-3-phenylpropyl)benzene 
• 1222135-24-1 1-[3-[5-[(2(S)-azetidinyl)methoxy]-3-pyridyl]phenyl]-3-phenyl-2(S)-propanol 
• 1222139-27-6 1-[3-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]phenyl]-3-phenyl-2(S)-propanol 
• 17131-14-5 (R)-3-phenylpropane-1,2-diol 

Relevant academic research and scientific papers

Asymmetric azidohydroxylation of styrene derivatives mediated by a biomimetic styrene monooxygenase enzymatic cascade

Enantioenriched azido alcohols are precursors for valuable chiral aziridines and 1,2-amino alcohols, however their chiral substituted analogues are difficult to access. We established a cascade for the asymmetric azidohydroxylation of styrene derivatives leading to chiral substituted 1,2-azido alcohols via enzymatic asymmetric epoxidation, followed by regioselective azidolysis, affording the azido alcohols with up to two contiguous stereogenic centers. A newly isolated two-component flavoprotein styrene monooxygenase StyA proved to be highly selective for epoxidation with a nicotinamide coenzyme biomimetic as a practical reductant. Coupled with azide as a nucleophile for regioselective ring opening, this chemo-enzymatic cascade produced highly enantioenriched aromatic α-azido alcohols with up to >99% conversion. A bi-enzymatic counterpart with halohydrin dehalogenase-catalyzed azidolysis afforded the alternative β-azido alcohol isomers with up to 94% diastereomeric excess. We anticipate our biocatalytic cascade to be a starting point for more practical production of these chiral compounds with two-component flavoprotein monooxygenases.

Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.

Production of enantiopure chiral epoxides with e. Coli expressing styrene monooxygenase

Styrene monooxygenases are a group of highly selective enzymes able to catalyse the epoxidation of alkenes to corresponding chiral epoxides in excellent enantiopurity. Chiral compounds containing oxirane ring or products of their hydrolysis represent key building blocks and precursors in organic synthesis in the pharmaceutical industry, and many of them are produced on an industrial scale. Two-component recombinant styrene monooxygenase (SMO) from Marinobacterium litorale was expressed as a fused protein (StyAL2StyB) in Escherichia coli BL21(DE3). By high cell density fermentation, 35 gDCW/L of biomass with overexpressed SMO was produced. SMO exhibited excellent stability, broad substrate specificity, and enantioselectivity, as it remained active for months and converted a group of alkenes to corresponding chiral epoxides in high enantiomeric excess (>95–99% ee). Optically pure (S)-4-chlorostyrene oxide, (S)-allylbenzene oxide, (2R,5R)-1,2:5,6-diepoxyhexane, 2-(3-bromopropyl)oxirane, and (S)-4-(oxiran-2-yl)butan-1-ol were prepared by whole-cell SMO.

A new monooxygenase from: Herbaspirillum huttiense catalyzed highly enantioselective epoxidation of allylbenzenes and allylic alcohols

Asymmetric epoxidation is a green route to enantiopure epoxides, but often suffers from low enantioselectivity toward unconjugated terminal alkenes. Mining of the NCBI non-redundant protein sequences with a reconstructed ancestral sequence based on six st

Synthesis of Seven-Membered Benzolactones by Nickel-Catalyzed C?H Coupling of Benzamides with Oxetanes

A NiCl2(PEt3)2-catalyzed regioselective C?H coupling of 8-aminoquinoline-derived benzamides with oxetanes has been developed. The reaction proceeds with concomitant removal of the 8-aminoquinoline auxiliary to directly for

Flexible tetrahydropyran synthesis from homopropargylic alcohols using sequential Pd-Au catalysis

A flexible synthetic method toward highly substituted tetrahydropyran is reported. The key transformation involves atom-efficient sequential metal catalysis consisting of Pd-catalyzed addition of homopropargylic alcohols to alkoxyallene and the subsequent

Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH

Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.

Nonenzymatic Regeneration of Styrene Monooxygenase for Catalysis

Styrene monooxygenase (SMO) is a two-component flavoprotein catalyzing the selective epoxidation of various C=C double bonds. For cell-free catalysis, traditionally a cascade of NAD(P)H:flavin oxidoreductase, nicotinamide cofactor (NADH), and NADH regener

AMIDE DERIVATIVES AS LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, formula (I) wherein R1. X, m. R2, Y, R3, Z, n, R4. A and B are as defined in the specification, processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

NOVEL COMPOUNDS

The present invention provides compounds of formula (I) and pharmaceutically acceptable salts thereof, wherein R1, X, m, R2, Y, R3, Z, n, R4, A and B are as defined in the specification, processes for their prep