BOC-5-BENZYLOXY-DL-TRYPTOPHAN

Base Information

• Chemical Name: BOC-5-BENZYLOXY-DL-TRYPTOPHAN
• CAS No.: 1219197-92-8
• Molecular Formula: C₂₃H₂₆N₂O₅
• Molecular Weight: 410.47
• Mol file: 1219197-92-8.mol

Synonyms:

Chemical Property of BOC-5-BENZYLOXY-DL-TRYPTOPHAN

Chemical Property:

Purity/Quality:

98%min ^*data from raw suppliers

Boc-5-benzyloxy-DL-tryptophan ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of BOC-5-BENZYLOXY-DL-TRYPTOPHAN

There total 5 articles about BOC-5-BENZYLOXY-DL-TRYPTOPHAN which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

(S)-methyl 3-(5-(benzyloxy)-1H-indol-3-yl)-2-((tert-butoxycarbonyl)amino)propanoate → (S)-3-(5-(benzyloxy)-1H-indol-3-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid (1219197-92-8)

Guidance literature:

With ethanol; sodium hydroxide; at 0 ℃; for 2h;

DOI:10.1021/jm401067s

Reference yield:

L-5-HTP (4350-09-8,4298-20-8) → (S)-3-(5-(benzyloxy)-1H-indol-3-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid (1219197-92-8)

Guidance literature:

Multi-step reaction with 4 steps

1: thionyl chloride / methanol / 0.17 h / 0 °C

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 20 °C

3: caesium carbonate / acetone / 20 °C

4: sodium hydroxide; ethanol / 2 h / 0 °C

With thionyl chloride; ethanol; caesium carbonate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In methanol; dichloromethane; acetone;

DOI:10.1021/jm401067s

Reference yield:

(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoate (203736-17-8,1234880-33-1) → (S)-3-(5-(benzyloxy)-1H-indol-3-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid (1219197-92-8)

Guidance literature:

Multi-step reaction with 2 steps

1: caesium carbonate / acetone / 20 °C

2: sodium hydroxide; ethanol / 2 h / 0 °C

With ethanol; caesium carbonate; sodium hydroxide; In acetone;

DOI:10.1021/jm401067s

upstream raw materials:

2-amino-3-(5-hydroxy-1H-indol-3-yl)propionic acid methyl ester

L-5-HTP

(S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(5-hydroxy-1H-indol-3-yl)propanoate

di-tert-butyl dicarbonate

Refernces

• 1、 Choi, Jun Yong,Calvet, Claudia M.,Gunatilleke, Shamila S.,Ruiz, Claudia,Cameron, Michael D.,McKerrow, James H.,Podust, Larissa M.,Roush, William R.. "Rational development of 4-aminopyridyl-based inhibitors targeting trypanosoma cruzi CYP51 as anti-chagas agents". . p. 7651 - 7668. Retrieved 2013/11/06.