32161-30-1

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dimethoxy-L-phenylalanine is used as a key intermediate for the synthesis of (2S)-2-amino-3-[3,4-di(methoxy)phenyl]propan-1-ol (β-amino alcohol), which is crucial in preparing the tetracyclic core of Erythrina alkaloids. These alkaloids have significant biological activities and are used in the development of various pharmaceutical products.
Used in Chemical Synthesis:
3,4-Dimethoxy-L-phenylalanine is also used as a reactant in the synthesis of 3-(3,4-Dimethoxyphenyl)-L-alanine, which is an important compound in the production of various chemical and pharmaceutical products.
Used in DOPA Production:
3,4-Dimethoxy-L-phenylalanine serves as an intermediate in the production of DOPA (3,4-Dihydroxyphenylalanine), a critical compound in the synthesis of neurotransmitters and hormones, as well as in the treatment of certain medical conditions.

InChI:InChI=1/C11H15NO4/c1-15-9-4-3-7(6-10(9)16-2)5-8(12)11(13)14/h3-4,6,8H,5,12H2,1-2H3,(H,13,14)/t8-/m0/s1

Upstream product

• 62682-18-2 DL-5-(3,4-dimethoxybenzyl)hydantoin 
• 141033-86-5 (S)-3-(3,4-Dimethoxy-phenyl)-2-[(1R,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-(2Z)-ylideneamino]-propionic acid (1S,2R,5S)-2-isopropyl-5-methyl-cyclohexyl ester 
• 59-92-7 levodopa 
• 77-78-1 dimethyl sulfate 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 2460-33-5 3,4-dimethoxyphenylpyruvic acid 
• 10040-91-2 5-(3,4-di-methoxybenzylidene)imidazolidine-2,4-dione 
• 27313-65-1 N-acetyl-3,4-dimethoxyphenylalanine 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 141895-37-6 (1S,2S,9S)-5-[1-(3,4-Dimethoxy-phenyl)-meth-(Z)-ylidene]-2,10,10-trimethyl-3-oxa-6-aza-tricyclo[7.1.1.0^2,7]undec-6-en-4-one 
• 40332-26-1 N-acetyl-3,4-dihydroxy-L-phenylalanine 
• 56771-16-5 2-amino-3-(3,4-dimethoxybenz-1-yl)propanoic acid methyl ester 
• 56-40-6 glycine 
• 7306-46-9 4-chloromethyl-1,2-dimethoxy-benzene 

Downstream Products

• 104528-83-8 (S)-(+)-3,4-dimethoxyphenylalanine ethyl ester 
• 80582-39-4 (2S)-2-amino-3-(3,4-dimethoxyphenyl)-1-propanol 
• 1162-02-3 15,16-Dimethoxy-cis-erythrinan-2,8-dion 
• 60723-34-4 15,16-Dimethoxy-cis-erythrinan-2,8-dion-2-ethylenacetal 
• 741266-34-2 11,12-dimethoxy-1,2,4a,5-tetrahydro-4H-indolo[7a,1-a]isoquinoline-3,6-dione 
• 741266-32-0 11,12-dimethoxy-3,6-dioxo-2,3,4,4a,5,6,8,9-octahydro-1H-indolo[7a,1-a]isoquinoline-8-carbaldehyde 
• 741266-28-4 C₂₁H₂₇NO₆ 
• 741266-30-8 8-hydroxymethyl-11,12-dimethoxy-1,2,4a,5,8,9-hexahydro-4H-indolo[7a,1-a]isoquinoline-3,6-dione 
• 26775-04-2 (9bS,13aS)-7,8-di(methoxy)-1,4,5,10,11,12,13,13a-octahydro-2H-indolo[7a,1-a]isoquinolin-2-one 
• 15248-47-2 (9bS,13aS)-7,8-di(methoxy)-1,4,5,10,11,12,13,13a-octahydro-2H-indolo[7a,1-a]isoquinoline 
• 489421-02-5 (9bS,13aS)-7,8-di(methoxy)-1,10,11,12,13,13a-hexahydro-2H-indolo[7a,1-a]isoquinolin-2-one 
• 489420-99-7 (3S,6aS,10aR)-3-{[3,4-di(methoxy)phenyl]methyl}perhydro[1,3]oxazolo[2,3-1]indol-5-one 
• 489421-01-4 (9bS,13aS)-7,8-di(methoxy)-2-oxo-1,4,5,10,11,12,13,13a-octahydro-2H-indolo[7a,1-a]isoquinolin-4-carbaldehyde 
• 489421-00-3 (4S,9bS,13aS)-4-(hydroxymethyl)-7,8-di(methoxy)-1,4,5,10,11,12,13,13a-octahydro-2H-indolo[7a,1-a]isoquinolin-2-one 

Relevant academic research and scientific papers

Synthesis method of 3-(3, 4-dimethoxyphenyl)-L-alanine

The invention relates to the technical field of chemical medicine intermediates, and provides a synthetic method of 3-(3, 4-dimethoxyphenyl)-L-alanine. The preparation method comprises the following steps: mixing water, veratraldehyde, ammonia water and hydantoin for condensation reaction to obtain condensation reaction liquid; ammonia water in the condensation reaction liquid is distilled out, residual feed liquid is directly subjected to a hydrogenation reduction reaction, and 3-(3, 4-dimethoxyphenyl)-L-alanine is obtained through alkaline hydrolysis and acidification. According to the method, the next step of reaction is directly carried out after ammonia water is evaporated from the condensation reaction liquid, the product of the condensation reaction does not need to be separated, the complicated post-treatment step after the condensation reaction is completed in the traditional method is avoided, the generation of three wastes is reduced, the environmental protection property is better, and meanwhile, the comprehensive yield of the target product is also improved. The result of the embodiment shows that when the 3-(3, 4-dimethoxyphenyl)-L-alanine is synthesized by adopting the method disclosed by the invention, the comprehensive yield of the product is 84 to 92 percent.

Chemoenzymatic synthesis of L-3,4-dimethoxyphenyl-alanine and its analogues using aspartate aminotransferase as a key catalyst

In this study, a chemoenzymatic synthesis method for the production of L-3,4-dimethoxyphenyl-alanine and its analogues from phenylpyruvate derivatives was developed. The aspartate aminotransferase from Escherichia coli was engineered by error prone PCR and the improved variants were identified. When 3, 4-dimethoxy phenylpyruvate was added by fed-batch on a preparative scale, L-3,4-dimethoxyphenyl-alanine was formed in 95.4% conversion and > 99% ee with the best aspartate aminotransferase variant as the catalyst. This study provided an efficient method for the production of methoxy substituted phenylalanines using the engineered aspartate aminotransferase.

Asymmetric synthesis of unnatural amino acids and tamsulosin chiral intermediate

An efficient and enantioselective hydrogenation of N-acetylamino phenyl acrylic acids was successfully developed by using ruthenium catalyst. This methodology is important in the field of pharmaceuticals and provides a new process for the preparation of unnatural amino acids and tamsulosin chiral intermediate.

Pictet-Spengler cyclization vs. Aminal formation: Competing reaction pathways of benzo[b][1,7]naphthyridines controlled by the configuration

Diastereoisomeric benzo[b][1,7]naphthyridines 13a,b were synthesized in nine steps from L-DOPA employing a Lewis acid-catalyzed cyclization of N-(4-methylpent-3-enyl)-a-amino aldehydes as the key step. Under aprotic Pictet-Spengler conditions, compounds 13a,b undergo different reaction pathways depending on the relative configuration. Whereas trans,cis-diastereoisomer 13a yielded the desired Pictet-Spengler cyclization product albeit in very low yield, the corresponding concave-shaped all-cis-diastereoisomer 13b undergoes intramolecular animal formation.

New synthetic amino acids for the design and synthesis of peptide-based metal ion sensors

The syntheses of two new nonstandard amino acids, Flu (6) and XBp (20), and a new synthesis of Dmd (12) are reported. These residues exhibit fluorescence, metal-coordination, and fluorescence-quenching properties, respectively. These building blocks have been incorporated into peptides via solid phase peptide synthesis to afford the prototype for a photoinduced electron transfer-based metal ion chemosensor. The fluorescence of the peptides is modulated upon metal binding. This results from a metal ion-induced conformational change that brings the side chains of the Flu and Dmd amino acids into proximity, thereby favoring photoinduced electron transfer (PET) fluorescence quenching.

Stereospecific syntheses of the lignans: 2-S-(3,4-dimethoxybenzyl)-3-R-(3,4,5-trimethoxybenzyl) butyrolactone, and its positional isomeric lactone

A short, versatile and stereospecific synthesis of two lignans 1 and 2, was achieved in 40% overall yield. Our strategy was based in the use of amino acids as chiral and readily available starting materials. Stereocontrolled transformation of amino acids to chiral organic phosphonates gave the key intermediate of the synthetic sequence. A Horner-Wadsworth-Emmons (HWE) reaction followed by selective reduction and stereospecific hydrogenation in the last step resulted in the title compounds with the desired absolute stereochemistry.

Efficient asymmetric synthesis of amino acids through hydrogenation of the didehydroamino acid residue in cyclic imino-ester derivatives

The trisubstituted olefinic bond of chiral cyclic α,β-didehydroamino acid derivatives was hydrogenated in the presence of Pd/C with >95% diastereoface discrimination to give, after hydrolysis, the corresponding S-amino acids. The reduction of the double bond with L-selectride does not change the orientation of diastereoface discrimination and the diastereoselectivity is still high.

Asymmetric synthesis X III: The stereocontrolled synthesis of (R)-α-amino acids via a double chiral induction

The stereocontrolled synthesis of (R)-α-amino acids via a double chiral induction in alkylation of the ketimine derived from (+)-camphor and (+)-methyl glycinate which is a chiral match pair has been studied. (R)-α-amino acids with high optical purity 80-90% are obtained after hydrolysis of the alkylated products. We find that the chiral match which is the synergistic effect in a double chiral induction is very important to obtain the higher diastereoselectivity for the stereocontrolled synthesis.

GENERAL METHOD FOR THE ASYMMETRIC SYNTHESIS OF α-AMINO ACIDS VIA ALKYLATION OF THE CHIRAL NICKEL(II) SCHIFF BASE COMPLEXES OF GLYCINE AND ALANINE

Nickel(II) complexes of Schiff bases derived from (S)-o-benzaldehyde and alanine (3), or (S)-O-benzophenone and alanine (4), or glycine (5) have been used for the asymmetric synthesis of α-amino acids under a variety of conditions.The method of choice consists of the reaction of the corresponding complex with the appropriate alkyl halide in DMF at 25 deg C using solid NaOH as a catalyst.Low diastereoselective excess (d.e.) is observed for the alkylation of complex (3) with benzyl bromide and allyl bromide.Large selectivity (80 percent) is observed for the alkylation of complex (4).Optically pure(R)- and (S)-O-benzyl-α-methyl-α-amino acids were obtained (70-90 percent) after the alkylated diastereoisomeric complexes had been seperated on SiO2 and hydrolysed with aqueous HCl.The initial chiral reagents were recovered (80-92 percent).The alkylation of complex (5) gave (S)-alanine, (S)-valine, (S)-phenylalanine, (S)-tryptophan, (S)-isoleucine, (S)-2-aminohexanoic acid, and 3,4-dimethoxyphenylalanine with optical yields of 70-92 percent.The optically pure α-amino acids were obtained after the separation of the alkylated diastereoisomeric complexes on SiO2.The stereochemical mechanism of the alkylation reaction is discussed.

Mechanism of Stereospecific Production of L-Amino Acids from the Corresponding 5-Substituted Hydantoins by Bacillus brevis

The mechanism of stereospecific production of L-amino acids from the corresponding 5-substituted hydantoins by Bacillus brevis AJ-12299 was studied.The enzymes involved in the reaction were partially purified by DEAE-Toyopearl 650M column chromatography and their properties were investigated.The conversion of DL-5-substituted hydantoins to the corresponding L-amino acids consisted of the following two successive reactions.The first step was the ring-opening hydrolysis to N-carbamoyl amino acids catalyzed by an ATP dependent L-5-substituted hydantoin hydrolase.This reaction was stereospecific and the N-carbamoyl amino acid produced was exclusively the L-form.N-Carbamoyl-L-amino acid was also produced from the D-form of 5-substituted hydantoin, which suggests that spontaneous racemization occurred in the reaction mixture.In the second step, N-carbamoyl-L-amino acid was hydrolyzed to L-amino acid by an N-carbamoyl-L-amino acid hydrolase, which was also an L-specific enzyme.The ATP dependency of the L-5-substituted hydantoin hydrolase was supposed to be the limiting factor in the production of L-amino acids from the corresponding 5-substituted hydantoins by this bacterium.