107447-04-1

Basic information

• Product Name: (S)-Methyl 2-aMino-3-(6-Methoxy-1H-indol-3-yl)propanoate
• Synonyms: (S)-Methyl 2-aMino-3-(6-Methoxy-1H-indol-3-yl)propanoate;methyl (S)-2-amino-3-(6-methoxy-1H-indol-3-yl)propanoate;6-Methoxy-L-tryptophan methyl ester;6-Methoxy-L-tryptophan methyl ester HCl
• CAS NO: 107447-04-1
• Molecular Formula: C₁₃H₁₆N₂O₃
• Molecular Weight: 248.27774
• Mol File: 107447-04-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-Methyl 2-aMino-3-(6-Methoxy-1H-indol-3-yl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-Methyl 2-aMino-3-(6-Methoxy-1H-indol-3-yl)propanoate(107447-04-1)
• EPA Substance Registry System: (S)-Methyl 2-aMino-3-(6-Methoxy-1H-indol-3-yl)propanoate(107447-04-1)

Safety Data

• Hazardous Substances Data: 107447-04-1(Hazardous Substances Data)

Usage

General Description

The chemical compound "(S)-Methyl 2-aMino-3-(6-Methoxy-1H-indol-3-yl)propanoate" is a derivative of the amino acid tryptophan. It is a methyl ester of a propanoic acid with an amino group attached to the second carbon and an indole group attached to the third carbon. The compound has a chiral center, and the (S)- prefix indicates that it has a specific spatial arrangement of atoms. The presence of the indole group suggests potential interactions with serotonin receptors in the body, and its methoxy group may also contribute to its pharmacological properties. (S)-Methyl 2-aMino-3-(6-Methoxy-1H-indol-3-yl)propanoate may have potential biological activities and may be of interest for research and pharmaceutical purposes.

Upstream product

• 1017238-28-6 (S)-methyl 2-{[(benzyloxy)carbonyl]amino}-3-(6-methoxy-1H-indol-3-yl)propanoate 
• 141215-69-2 methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate 
• 72458-78-7 8-acetyl-6-methoxy-1,2-dimethoxycarbonylpyrrolo<2,3-b>indole 
• 67811-39-6 (2S,3aR)-8-Acetyl-3,3a,8,8a-tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dimethyl ester 
• 123287-67-2 N_b-methoxycarbonyl-6-methoxy-L-tryptophan methyl ester 
• 3189-13-7 6-methoxylindole 

Downstream Products

• 111427-92-0 (1S,3S)-7-Methoxy-1-(2-methyl-2-phenylsulfanyl-propyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 111427-93-1 (1R,3S)-7-Methoxy-1-(2-methyl-2-phenylsulfanyl-propyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 107447-05-2 (1S,3S)-methyl-1-isobutyl-7-methoxy-2,3,4,9-tetrahydro-1H-beta-carboline-3-carboxylate 
• 1699720-85-8 (3S,6S,12aS)-6-isobutyl-9-methoxy-3-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione 
• 12771-72-1 verruculogen 
• 12626-18-5 Fumitremorgin A 
• 111139-38-9 fumitremorgin B 
• 111433-90-0 (1S,3S)-7-Methoxy-1-(2-methyl-2-phenylsulfanyl-propyl)-2-[(S)-1-(2,2,2-trichloro-ethoxycarbonyl)-pyrrolidine-2-carbonyl]-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 116611-97-3 (S)-2-{(S)-1-Methoxycarbonyl-2-[6-methoxy-2-(3-methyl-3-phenylsulfanyl-butyryl)-1H-indol-3-yl]-ethylcarbamoyl}-pyrrolidine-1-carboxylic acid 2,2,2-trichloro-ethyl ester 
• 111427-94-2 (S)-7-Methoxy-1-(2-methyl-2-phenylsulfanyl-propyl)-2-[(S)-1-(2,2,2-trichloro-ethoxycarbonyl)-pyrrolidine-2-carbonyl]-2,9-dihydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 107462-41-9 (1S,3S)-2-((S)-1-Benzyloxycarbonyl-pyrrolidine-2-carbonyl)-1-isobutyl-7-methoxy-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester 
• 208761-40-4 C₂₈H₃₁N₃O₅S 
• 208761-39-1 C₂₈H₃₁N₃O₄S 

Relevant articles and documents

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Total synthesis of verruculogen and fumitremorgin a enabled by ligand-controlled C-H borylation

Verruculogen and fumitremorgin A are bioactive alkaloids that contain a unique eight-membered endoperoxide. Although related natural products such as fumitremorgins B and C have been previously synthesized, we report the first synthesis of the more complex, endoperoxide-containing members of this family. A concise route to verruculogen and fumitremorgin A relied not only on a hydroperoxide/indole hemiaminal cyclization, but also on the ability to access the seemingly simple starting material, 6-methoxytryptophan. An iridium-catalyzed C-H borylation/Chan-Lam procedure guided by an N-TIPS group enabled the conversion of a tryptophan derivative into a 6-methoxytryptophan derivative, proving to be a general way to functionalize the C6 position of an N,C3-disubstituted indole for the synthesis of indole-containing natural products and pharmaceuticals.

Synthetic Approaches to Fumitremorgins. III. Synthesis of Optically Active Pentacyclic Ring Systems, and Their Oxidation at Ring C

Pictet-Spengler reaction of L-tryptophan methyl ester (9) and 6-methoxy-L-tryptophan methyl ester (40) with isovaleraldehyde (10) in methylene chloride in the presence of trifluoroacetic acid gave the cis-tetrahydro-β-carboline (11, 41) as the major isome