5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-20α-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole

Base Information

• Chemical Name: 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-20α-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole
• CAS No.: 1335144-50-7
• Molecular Formula: C₄₆H₅₂N₄O₆S₂
• Molecular Weight: 821.074

Synonyms:5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-20α-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole

Chemical Property of 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-20α-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole

Chemical Property:

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Technology Process of 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-20α-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole

There total 4 articles about 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-20α-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole 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: 7.0%

5-methyl-5-[4-(2-methoxycarbonylethyl-1-thio)phenyl]dipyrromethane (1335144-47-2) + 5-methyl-5-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]dipyrromethane (1335144-48-3) + acetone (67-64-1) → 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α,20β-bis-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole (1335144-53-0) + 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α,20α-bis-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole (1335144-49-4) + 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-20β-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole (1335144-54-1) + 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-20α-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole (1335144-50-7) + 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α,20β-bis[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-calix[4]pyrrole (1335144-55-2) + 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α,20α-bis[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-calix[4]pyrrole (1335144-52-9)

Guidance literature:

5-methyl-5-[4-(2-methoxycarbonylethyl-1-thio)phenyl]dipyrromethane; 5-methyl-5-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]dipyrromethane; acetone; With trifluoroacetic acid; at 0 - 20 ℃; for 1h; Inert atmosphere;

With sodium hydroxide;

DOI:10.1016/j.tet.2011.07.082

Reference yield:

4-mercaptoacetophenone (3814-20-8) → 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-20β-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole (1335144-54-1) + 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-20α-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole (1335144-50-7)

Guidance literature:

Multi-step reaction with 4 steps

1: N-benzyl-trimethylammonium hydroxide / tetrahydrofuran; methanol / -78 - 20 °C / Inert atmosphere

2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -78 °C

3: trifluoroacetic acid / 1.5 h / 0 - 20 °C / Inert atmosphere

4: trifluoroacetic acid / 1 h / 0 - 20 °C / Inert atmosphere

With N-benzyl-trimethylammonium hydroxide; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tet.2011.07.082

Reference yield:

3-[(4-acetylphenyl)thio]-propanoic acid methyl ester (1153277-69-0) → 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-20β-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole (1335144-54-1) + 5,10,15,20,22,24-hexahydro-5,5,10,15,15,20-hexamethyl-10α-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]-20α-[4-(2-methoxycarbonylethyl-1-thio)phenyl]-calix[4]pyrrole (1335144-50-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / -78 °C

2: trifluoroacetic acid / 1.5 h / 0 - 20 °C / Inert atmosphere

3: trifluoroacetic acid / 1 h / 0 - 20 °C / Inert atmosphere

With 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.tet.2011.07.082

upstream raw materials:

5-methyl-5-[4-(2-methoxycarbonylethyl-1-thio)phenyl]dipyrromethane

5-methyl-5-[4-(2-methoxycarbonylethyl-1-sulfonyl)phenyl]dipyrromethane

acetone

3-[(4-acetylphenyl)thio]-propanoic acid methyl ester

Downstream raw materials:

C₆H₄NO₃^(1-)*C₄₆H₅₂N₄O₆S₂*Cs⁽¹⁺⁾

C₆H₅O^(1-)*C₄₆H₅₂N₄O₆S₂*Cs⁽¹⁺⁾

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