Benzyl 13,17-bis-(2-methoxycarbonylethyl)-12,18-bis-(methoxycarbonylmethyl)-2,2,8,8-tetramethylisobacteriochlorin-5-carboxylate

Base Information

• Chemical Name: Benzyl 13,17-bis-(2-methoxycarbonylethyl)-12,18-bis-(methoxycarbonylmethyl)-2,2,8,8-tetramethylisobacteriochlorin-5-carboxylate
• CAS No.: 145045-93-8
• Molecular Formula: C₄₆H₅₂N₄O₁₀
• Molecular Weight: 820.94
• Mol file: 145045-93-8.mol

Synonyms:

Chemical Property of Benzyl 13,17-bis-(2-methoxycarbonylethyl)-12,18-bis-(methoxycarbonylmethyl)-2,2,8,8-tetramethylisobacteriochlorin-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzyl 13,17-bis-(2-methoxycarbonylethyl)-12,18-bis-(methoxycarbonylmethyl)-2,2,8,8-tetramethylisobacteriochlorin-5-carboxylate

There total 7 articles about Benzyl 13,17-bis-(2-methoxycarbonylethyl)-12,18-bis-(methoxycarbonylmethyl)-2,2,8,8-tetramethylisobacteriochlorin-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:

t-butyl 1,2,3,10-tetrahydro-8-(2-methoxycarbonylethyl)-7-methoxycarbonylmethyl-3,3-dimethyl-1-thioxodipyrrin-9-carboxylate (145045-86-9) → Benzyl 13,17-bis-(2-methoxycarbonylethyl)-12,18-bis-(methoxycarbonylmethyl)-2,2,8,8-tetramethylisobacteriochlorin-5-carboxylate (145045-93-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / DBU / CH₂Cl₂ / 1.08 h

2: 82.5 percent / DBU, Ph₃P / toluene / 1 h / Heating

3: 35 percent / Bu₄NF / tetrahydrofuran / 17 h / 50 °C

4: CF₃CO₂H / 2.5 h

5: 1) trimethyl orthoformate, CF₃CO₂H / 1) MeOH, 10 min, 2) THF, 96 h, irradiation

With tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; trifluoroacetic acid; trimethyl orthoformate; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1039/P19920002175

Reference yield:

2-[5-[1-[5-tert-Butoxycarbonyl-4-(2-methoxycarbonyl-ethyl)-3-methoxycarbonylmethyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-4,4-dimethyl-pyrrolidin-(2Z)-ylidene]-malonic acid benzyl ester 2-trimethylsilanyl-ethyl ester (145045-89-2,145046-05-5) → Benzyl 13,17-bis-(2-methoxycarbonylethyl)-12,18-bis-(methoxycarbonylmethyl)-2,2,8,8-tetramethylisobacteriochlorin-5-carboxylate (145045-93-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 35 percent / Bu₄NF / tetrahydrofuran / 17 h / 50 °C

2: CF₃CO₂H / 2.5 h

3: 1) trimethyl orthoformate, CF₃CO₂H / 1) MeOH, 10 min, 2) THF, 96 h, irradiation

With tetrabutyl ammonium fluoride; trifluoroacetic acid; trimethyl orthoformate; In tetrahydrofuran;

DOI:10.1039/P19920002175

Reference yield:

2-{5-[1-[5-tert-Butoxycarbonyl-4-(2-methoxycarbonyl-ethyl)-3-methoxycarbonylmethyl-1H-pyrrol-2-yl]-meth-(Z)-ylidene]-4,4-dimethyl-4,5-dihydro-3H-pyrrol-2-ylsulfanyl}-malonic acid benzyl ester 2-trimethylsilanyl-ethyl ester (145045-88-1) → Benzyl 13,17-bis-(2-methoxycarbonylethyl)-12,18-bis-(methoxycarbonylmethyl)-2,2,8,8-tetramethylisobacteriochlorin-5-carboxylate (145045-93-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 82.5 percent / DBU, Ph₃P / toluene / 1 h / Heating

2: 35 percent / Bu₄NF / tetrahydrofuran / 17 h / 50 °C

3: CF₃CO₂H / 2.5 h

4: 1) trimethyl orthoformate, CF₃CO₂H / 1) MeOH, 10 min, 2) THF, 96 h, irradiation

With tetrabutyl ammonium fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; trifluoroacetic acid; trimethyl orthoformate; In tetrahydrofuran; toluene;

DOI:10.1039/P19920002175

upstream raw materials:

5-<5-formyl-4-(2-methoxycarbonylethyl)-3-methoxycarbonylmethylpyrrol-2-ylmethylene>-3,4-dihydro-2-methoxy-4,4-dimethylpyrrole

3-{5-[5-[1-Benzyloxycarbonyl-meth-(E)-ylidene]-3,3-dimethyl-pyrrolidin-(2Z)-ylidenemethyl]-4-methoxycarbonylmethyl-1H-pyrrol-3-yl}-propionic acid methyl ester

t-butyl 1,2,3,10-tetrahydro-8-(2-methoxycarbonylethyl)-7-methoxycarbonylmethyl-3,3-dimethyl-1-thioxodipyrrin-9-carboxylate

tert-Butyl (4Z)-1-benzyloxycarbonylmethylene-8-(2-methoxycarbonylethyl)-7-methoxycarbonylmethyl-3,3-dimethyl-1,2,3,10-tetrahydrodipyrrin-9-carboxylate