3-[5-[[3-(2-carboxyethyl)-5-[[3-(2-carboxyethyl)-5-[[3-(2-carboxyethyl)-5-(carboxymethyl)-4-(hydroxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid

Base Information

• Chemical Name: 3-[5-[[3-(2-carboxyethyl)-5-[[3-(2-carboxyethyl)-5-[[3-(2-carboxyethyl)-5-(carboxymethyl)-4-(hydroxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid
• CAS No.: 71861-60-4
• Molecular Formula: C40H46 N4 O17
• Molecular Weight: 854.822
• Mol file: 71861-60-4.mol

Synonyms:3-[5-[[3-(2-carboxyethyl)-5-[[3-(2-carboxyethyl)-5-[[3-(2-carboxyethyl)-5-(carboxymethyl)-4-(hydroxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid;21H-Biline-2,7,12,17-tetrapropanoic acid, 3,8,13,18-tetrakis(carboxymethyl)-5,10,15,22,23,24-hexahydro-19-(hydroxymethyl)-

Chemical Property of 3-[5-[[3-(2-carboxyethyl)-5-[[3-(2-carboxyethyl)-5-[[3-(2-carboxyethyl)-5-(carboxymethyl)-4-(hydroxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1135.6°C at 760 mmHg
• Flash Point: 640.6°C
• PSA: 381.79000
• Density: 1.582g/cm³
• LogP: 1.84090
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 13
• Hydrogen Bond Acceptor Count: 17
• Rotatable Bond Count: 27
• Exact Mass: 854.28579601
• Heavy Atom Count: 61
• Complexity: 1600

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=C(N1)CC2=C(C(=C(N2)CC3=C(C(=C(N3)CC4=C(C(=C(N4)CC(=O)O)CO)CCC(=O)O)CC(=O)O)CCC(=O)O)CC(=O)O)CCC(=O)O)CC(=O)O)CCC(=O)O

Technology Process of 3-[5-[[3-(2-carboxyethyl)-5-[[3-(2-carboxyethyl)-5-[[3-(2-carboxyethyl)-5-(carboxymethyl)-4-(hydroxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid

There total 13 articles about 3-[5-[[3-(2-carboxyethyl)-5-[[3-(2-carboxyethyl)-5-[[3-(2-carboxyethyl)-5-(carboxymethyl)-4-(hydroxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-2-yl]methyl]-4-(carboxymethyl)-1H-pyrrol-3-yl]propanoic acid 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:

benzyl 5'-formyl-4,3'-di(2-methoxycarbonylethyl)-3,4'-bismethoxy-carbonylmethyl-2,2'-methylenedipyrrole-5-carboxylate (71015-84-4) → 3,8,13,18-tetra-(2-carboxyethyl)-2,7,12,17-tetrakiscarboxymethyl-1-hydroxymethylbilane (71861-60-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / Et₃N, H₂ / Pd/C / tetrahydrofuran / Ambient temperature

2: 69 percent / NaHCO₃, iodine, potassium iodide / H₂O; CH₂Cl₂

3: 72 percent / H₂, Et₃N / Adams' platinum oxide / methanol / 0.75 h / 20 °C

4: 56 percent / acetic acid / 20 °C

5: 80 percent / sodium borohydride, Et₃N / CHCl₃; methanol

6: aq. KOH / 16 h / 25 °C

With potassium hydroxide; sodium tetrahydroborate; hydrogen; iodine; sodium hydrogencarbonate; acetic acid; triethylamine; potassium iodide; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; water;

DOI:10.1039/P19820002427

Reference yield:

3-{5-Formyl-2-[5-iodo-4-(2-methoxycarbonyl-ethyl)-3-methoxycarbonylmethyl-1H-pyrrol-2-ylmethyl]-4-methoxycarbonylmethyl-1H-pyrrol-3-yl}-propionic acid methyl ester (84290-88-0) → 3,8,13,18-tetra-(2-carboxyethyl)-2,7,12,17-tetrakiscarboxymethyl-1-hydroxymethylbilane (71861-60-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 72 percent / H₂, Et₃N / Adams' platinum oxide / methanol / 0.75 h / 20 °C

2: 56 percent / acetic acid / 20 °C

3: 80 percent / sodium borohydride, Et₃N / CHCl₃; methanol

4: aq. KOH / 16 h / 25 °C

With potassium hydroxide; sodium tetrahydroborate; hydrogen; acetic acid; triethylamine; platinum(IV) oxide; In methanol; chloroform;

DOI:10.1039/P19820002427

Reference yield:

5'-formyl-3',4-di-(2-methoxycarbonylethyl)-3,4'-dimethoxycarbonylmethyl-2,2'-methylenedipyrrole-5-carboxylic acid (84290-87-9) → 3,8,13,18-tetra-(2-carboxyethyl)-2,7,12,17-tetrakiscarboxymethyl-1-hydroxymethylbilane (71861-60-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 69 percent / NaHCO₃, iodine, potassium iodide / H₂O; CH₂Cl₂

2: 72 percent / H₂, Et₃N / Adams' platinum oxide / methanol / 0.75 h / 20 °C

3: 56 percent / acetic acid / 20 °C

4: 80 percent / sodium borohydride, Et₃N / CHCl₃; methanol

5: aq. KOH / 16 h / 25 °C

With potassium hydroxide; sodium tetrahydroborate; hydrogen; iodine; sodium hydrogencarbonate; acetic acid; triethylamine; potassium iodide; platinum(IV) oxide; In methanol; dichloromethane; chloroform; water;

DOI:10.1039/P19820002427

upstream raw materials:

C₄₈H₆₂N₄O₁₇

benzyl 5'-formyl-4,3'-di(2-methoxycarbonylethyl)-3,4'-bismethoxy-carbonylmethyl-2,2'-methylenedipyrrole-5-carboxylate

5'-formyl-4,3'-di-(2-methoxycarbonylethyl)-3,4'-bismethoxycarbonylmethyl-2,2'-methylenedipyrrole

3-{5-Hydroxymethyl-2-[4-(2-methoxycarbonyl-ethyl)-3-methoxycarbonylmethyl-1H-pyrrol-2-ylmethyl]-4-methoxycarbonylmethyl-1H-pyrrol-3-yl}-propionic acid methyl ester

Downstream raw materials:

protoporphyrin IX

coproporphyrinogen III

uroporphyrinogen I

uroporphyrinogen III

Refernces

• 1、 Donegan, Rebecca K.,Moore, Courtney M.,Hanna, David A.,Reddi, Amit R.. "Handling heme: The mechanisms underlying the movement of heme within and between cells". . p. 88 - 100. Retrieved 2018/08/21.