tert-butyl 3,3'-bis<(methoxycarbonyl)methyl>-4,4'-bis<β-(methoxycarbonyl)ethyl>-5-<(benzyloxy)carbonyl>dipyrrylmethane-5-carboxylate

Base Information

• Chemical Name: tert-butyl 3,3'-bis<(methoxycarbonyl)methyl>-4,4'-bis<β-(methoxycarbonyl)ethyl>-5-<(benzyloxy)carbonyl>dipyrrylmethane-5-carboxylate
• CAS No.: 75975-54-1
• Molecular Formula: C₃₆H₄₄N₂O₁₂
• Molecular Weight: 696.752
• Mol file: 75975-54-1.mol

Synonyms:tert-butyl 3,3'-bis<(methoxycarbonyl)methyl>-4,4'-bis<β-(methoxycarbonyl)ethyl>-5-<(benzyloxy)carbonyl>dipyrrylmethane-5-carboxylate

Chemical Property of tert-butyl 3,3'-bis<(methoxycarbonyl)methyl>-4,4'-bis<β-(methoxycarbonyl)ethyl>-5-<(benzyloxy)carbonyl>dipyrrylmethane-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 3,3'-bis<(methoxycarbonyl)methyl>-4,4'-bis<β-(methoxycarbonyl)ethyl>-5-<(benzyloxy)carbonyl>dipyrrylmethane-5-carboxylate

There total 7 articles about tert-butyl 3,3'-bis<(methoxycarbonyl)methyl>-4,4'-bis<β-(methoxycarbonyl)ethyl>-5-<(benzyloxy)carbonyl>dipyrrylmethane-5-carboxylate 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: 62.0%

3-(2-Methoxycarbonyl-ethyl)-4-methoxycarbonylmethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester (75975-52-9) + 5-acetoxymethyl-3-(2-methoxycarbonyl-ethyl)-4-methoxycarbonylmethyl-pyrrole-2-carboxylic acid benzyl ester (50622-67-8) → tert-butyl 3,3'-bis<(methoxycarbonyl)methyl>-4,4'-bis<β-(methoxycarbonyl)ethyl>-5-<(benzyloxy)carbonyl>dipyrrylmethane-5-carboxylate (75975-54-1)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 41 ℃; for 5h;

DOI:10.1021/jo00318a008

Reference yield:

3-(2-methoxycarbonyl-ethyl)-4-methoxycarbonylmethyl-pyrrole-2-carboxylic acid benzyl ester (50622-60-1) + tert-Butyl 5-acetoxymethyl-3-(2-methoxycarbonylethyl)-4-methoxycarbonylmethylpyrrole-2-carboxylate (70988-60-2) → tert-butyl 3,3'-bis<(methoxycarbonyl)methyl>-4,4'-bis<β-(methoxycarbonyl)ethyl>-5-<(benzyloxy)carbonyl>dipyrrylmethane-5-carboxylate (75975-54-1) + 3,3'-bis-(2-methoxycarbonyl-ethyl)-4,4'-bis-methoxycarbonylmethyl-1H,1'H-5,5'-methanediyl-bis-pyrrole-2-carboxylic acid dibenzyl ester (55305-15-2)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 1.75h; Ambient temperature;

Reference yield:

4-<2-(methoxycarbonyl)ethyl>-3-<(methoxycarbonyl)methyl>pyrrole-5-carboxylic acid (75993-22-5) → tert-butyl 3,3'-bis<(methoxycarbonyl)methyl>-4,4'-bis<β-(methoxycarbonyl)ethyl>-5-<(benzyloxy)carbonyl>dipyrrylmethane-5-carboxylate (75975-54-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.7 g / dicyclohexylcarbodiimide / tetrahydrofuran / 17 h / 20 °C

2: 62 percent / p-toluenesulfonic acid / CH₂Cl₂ / 5 h / 41 °C

With toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00318a008

upstream raw materials:

3-(2-Methoxycarbonyl-ethyl)-4-methoxycarbonylmethyl-1H-pyrrole-2-carboxylic acid tert-butyl ester

5-acetoxymethyl-3-(2-methoxycarbonyl-ethyl)-4-methoxycarbonylmethyl-pyrrole-2-carboxylic acid benzyl ester

3-(2-methoxycarbonyl-ethyl)-4-methoxycarbonylmethyl-pyrrole-2-carboxylic acid benzyl ester

tert-Butyl 5-acetoxymethyl-3-(2-methoxycarbonylethyl)-4-methoxycarbonylmethylpyrrole-2-carboxylate

Downstream raw materials:

uroporphyrinogen III

uroporphyrinogen II

5,5-bis[5-benzyloxycarbonyl-4-(2-methoxycarbonylethyl)-3-methoxycarbonylmethylpyrrol-2-ylmethyl]-3-(2-methoxycarbonylethyl)-4-methoxycarbonylmethyl-1H-pyrrol-2(5H)-one

5-[5-Iodo-4-(2-methoxycarbonyl-ethyl)-3-methoxycarbonylmethyl-1H-pyrrol-2-ylmethyl]-3-(2-methoxycarbonyl-ethyl)-4-methoxycarbonylmethyl-1H-pyrrole-2-carboxylic acid benzyl ester