N-[(Phenylmethoxy)carbonyl]-D-tryptophan phenylmethyl ester

Base Information

• Chemical Name: N-[(Phenylmethoxy)carbonyl]-D-tryptophan phenylmethyl ester
• CAS No.: 126496-81-9
• Molecular Formula: C26H24N2O4
• Molecular Weight: 428.47976
• Mol file: 126496-81-9.mol

Synonyms:N-[(Phenylmethoxy)carbonyl]-D-tryptophan phenylmethyl ester

Chemical Property of N-[(Phenylmethoxy)carbonyl]-D-tryptophan phenylmethyl ester

Chemical Property:

• Boiling Point: 656.7±55.0 °C(Predicted)
• PKA: 10.93±0.46(Predicted)
• PSA: 80.42000
• Density: 1.266
• LogP: 5.13970
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

benzyl((benzyloxy)carbonyl)-D-tryptophanate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-[(Phenylmethoxy)carbonyl]-D-tryptophan phenylmethyl ester

There total 3 articles about N-[(Phenylmethoxy)carbonyl]-D-tryptophan phenylmethyl ester 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: 33.0%

indole (120-72-9) + benzyl (2R)-1-benzyloxycarbonyl-2-aziridinecarboxylate (86122-63-6) → (R)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionic acid benzyl ester (126496-81-9)

Guidance literature:

With zinc trifluoromethanesulfonate; In chloroform; at 78 ℃; for 18h;

DOI:10.1016/S0040-4039(00)99325-0

Reference yield:

(R)-1-Trityl-aziridine-2-carboxylic acid benzyl ester (126496-78-4) → (R)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionic acid benzyl ester (126496-81-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) TFA

2: 33 percent / Zn(OTf)2 / CHCl₃ / 18 h / 78 °C

With zinc trifluoromethanesulfonate; trifluoroacetic acid; In chloroform;

DOI:10.1016/S0040-4039(00)99325-0

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (R)-2-Benzyloxycarbonylamino-3-(1H-indol-3-yl)-propionic acid benzyl ester (126496-81-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) TFA

2: 33 percent / Zn(OTf)2 / CHCl₃ / 18 h / 78 °C

With zinc trifluoromethanesulfonate; trifluoroacetic acid; In chloroform;

DOI:10.1016/S0040-4039(00)99325-0

upstream raw materials:

indole

benzyl (2R)-1-benzyloxycarbonyl-2-aziridinecarboxylate

(R)-1-Trityl-aziridine-2-carboxylic acid benzyl ester

benzyl chloroformate

Downstream raw materials:

(2R,3aS,8aS)-3,3a,8,8a-Tetrahydro-2H-pyrrolo[2,3-b]indole-1,2-dicarboxylic acid dibenzyl ester

α-methyl-DL-tryptophan

3-((R)-2-Benzyloxycarbonyl-2-benzyloxycarbonylamino-propyl)-indole-1-carboxylic acid benzyl ester

(2R,3aS,8aR)-2,3,3a,8a-Tetrahydro-pyrrolo[2,3-b]indole-1,2,8-tricarboxylic acid tribenzyl ester

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