130812-44-1

Basic information

• Product Name: Cbz-D-Tryptophan methyl ester
• Synonyms: (R)-methyl 2-(benzyloxycarbonylamino)-3-(1H-indol-3-yl)propanoate;Cbz-D-Tryptophan methyl ester;Z-D-Trp-OMe;Cbz-D-Trp.ome
• CAS NO: 130812-44-1
• Molecular Formula: C₂₀H₂₀N₂O₄
• Molecular Weight: 352.3838
• Mol File: 130812-44-1.mol
• Article Data: 24

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cbz-D-Tryptophan methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Cbz-D-Tryptophan methyl ester(130812-44-1)
• EPA Substance Registry System: Cbz-D-Tryptophan methyl ester(130812-44-1)

Safety Data

• Hazardous Substances Data: 130812-44-1(Hazardous Substances Data)

Usage

General Description

Cbz-D-Tryptophan methyl ester is a chemical compound that is a derivative of the amino acid tryptophan. It is used in chemical and pharmaceutical research for its potential therapeutic applications. The "Cbz" prefix stands for carbobenzyloxy, indicating the presence of a protecting group on the amino group of tryptophan. The methyl ester group serves as a protective group for the carboxylic acid functionality. Cbz-D-Tryptophan methyl ester can be used in the synthesis of peptide-based drugs and can also be utilized in the study of protein structure and function. Its unique chemical structure and properties make it a valuable tool in scientific research and drug development.

Upstream product

• 7432-21-5 N-carbobenzyloxy-L-tryptophane 
• 74-88-4 methyl iodide 
• 73-22-3 L-Tryptophan 
• 14907-27-8 (R)-(+)-tryptophan methyl ester hydrochloride 
• 501-53-1 benzyl chloroformate 
• 153-94-6 D-tryptophan 
• 67-56-1 methanol 
• 2279-15-4 N-(benzyloxycarbonyl)-D-tryptophan 
• 186581-53-3 diazomethane 
• 120-72-9 indole 
• 104597-98-0 (S)-2-methoxycarbonyl-1-benzyloxycarbonylaziridine 
• 4299-70-1 L-tryptophan methyl ester 
• 1053208-94-8 N-carbobenzyloxy-2-iodo-L-tryptophan methyl ester 
• 13139-17-8 N-(Benzyloxycarbonyloxy)succinimide 

Downstream Products

• 169687-64-3 (2S,3aR,8aR)-3,3a,8,8a-Tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 
• 130680-69-2 Cbz-ΔTrp-OMe 
• 84590-48-7 indolactam V 
• 110815-32-2 (S)-(2-(4-amino-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester 
• 110815-28-6 (R)-(1-((acetoxy)methyl)-2-(1H-indol-3-yl)-2-oxoethyl)carbamic acid phenylmethyl ester 
• 110815-31-1 Acetic acid (R)-3-(4-amino-1H-indol-3-yl)-2-benzyloxycarbonylamino-3-oxo-propyl ester 
• 110815-29-7 Acetic acid (R)-2-benzyloxycarbonylamino-3-(4-nitro-1H-indol-3-yl)-3-oxo-propyl ester 
• 110815-30-0 Acetic acid (R)-2-benzyloxycarbonylamino-3-(6-nitro-1H-indol-3-yl)-3-oxo-propyl ester 
• 110815-33-3 2-[3-((S)-2-Benzyloxycarbonylamino-3-hydroxy-propyl)-1H-indol-4-ylamino]-3-methyl-butyric acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 84590-48-7 (+)-Epi-indolactam-V 
• 110815-27-5 (S)-(2-acetoxy)-1-((1H-indol-3-ylmethyl)ethyl)carbamic acid, phenylmethyl ester 
• 131442-94-9 (S,S)-(2-(4-((1-(((phenylmethyl)oxy)carbonyl)-2-methylpropyl)amino)-1H-indol-3-yl)-1-(hydroxymethyl)ethyl)carbamic acid, phenylmethyl ester 
• 1146633-44-4 (2S)-2-(benzyloxycarbonylamino)-3-(3-fluoro-2-oxoindoline-3-yl)propionic acid methyl ester 
• 1053209-02-1 N-carbobenzyloxy-1-acetyl-L-tryptophan methyl ester 

Relevant articles and documents

Scandium perchlorate as a superior Lewis acid for regioselective ring opening of aziridine carboxylate with indoles

In the synthesis of optically active tryptophan derivatives, Lewis acid-promoted coupling between indole and optically active serine-derived aziridine carboxylate is attractive because of the flexibility and convergence. Scandium perchlorate has been found to be a superior Lewis acid to the previously reported scandium triflate with respect to the yields as well as the regioselectivity of aziridine ring opening. The scope and limitation of this Lewis acid are also described.

Method for preparing pharmaceutical intermediate of tryptophan derivative

The synthesis method comprises the following steps: L - tryptophan derivatives are taken as starting materials, and esterification is carried out in sequence. The amidation, Boc protection, hydrolysis, amidation or sequential esterification, amidation, Boc protection, hydrogenation, hydrolysis, amidation yields a target product, a tryptophan derivative pharmaceutical intermediate. The preparation method has the advantages of cheap and easily available raw materials, environment friendliness, less process three wastes, accords with the idea of green pharmacy, mild reaction conditions, simple process, simple and convenient operation, high yield and purity and easy amplification and production.

Synthesis of 10b-fluorinated analogues of protubonine a and its 11a-epimer via fluorocyclisation of tryptophan-containing dipeptides

The synthesis of 10b-fluorinated analogues of protubonine A and its 11a-epimer was accomplished using fluorocyclisation of tryptophan-containing dipeptides with N-fluoro-2,4,6-trimethylpyridinium triflate to 3a-fluoropyrrolo[2,3-b]indoles as a key step. Acetylation of the indole nitrogen and the following diketopiperazine formation gave the 10b-fluorinated analogues of protubonine A and its 11a-epimer.