Methanesulfonic acid (E)-(R)-1-[(S)-1-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-2-((S)-toluene-4-sulfinyl)-but-2-enyl ester

Base Information

• Chemical Name: Methanesulfonic acid (E)-(R)-1-[(S)-1-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-2-((S)-toluene-4-sulfinyl)-but-2-enyl ester
• CAS No.: 172376-24-8
• Molecular Formula: C₃₄H₅₀O₅S₂
• Molecular Weight: 602.9

Synonyms:

Chemical Property of Methanesulfonic acid (E)-(R)-1-[(S)-1-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-2-((S)-toluene-4-sulfinyl)-but-2-enyl ester

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Technology Process of Methanesulfonic acid (E)-(R)-1-[(S)-1-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-2-((S)-toluene-4-sulfinyl)-but-2-enyl ester

There total 3 articles about Methanesulfonic acid (E)-(R)-1-[(S)-1-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-2-((S)-toluene-4-sulfinyl)-but-2-enyl 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: 82.0%

(+)-(22R,23E,RS)-22-hydroxy-6β-methoxy-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-26,27-dinorcholest-23-ene (172376-22-6) + Methanesulfonic anhydride (7143-01-3) → Methanesulfonic acid (E)-(R)-1-[(S)-1-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-2-((S)-toluene-4-sulfinyl)-but-2-enyl ester (172376-24-8)

Guidance literature:

With pyridine; for 3h; 0 deg C -> room temperature;

DOI:10.1021/jo951264k

Reference yield:

(R,E)-1-methyl-4-(prop-1-en-1-ylsulfinyl)benzene (156767-62-3) → Methanesulfonic acid (E)-(R)-1-[(S)-1-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-2-((S)-toluene-4-sulfinyl)-but-2-enyl ester (172376-24-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 1.5 h

2: 82 percent / pyridine / 3 h / 0 deg C -> room temperature

With pyridine; lithium diisopropyl amide;

DOI:10.1021/jo951264k

Reference yield:

(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde (25819-77-6) → Methanesulfonic acid (E)-(R)-1-[(S)-1-((1aR,3aR,3bS,5aS,6R,8aS,8bS,10R,10aR)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-6-yl)-ethyl]-2-((S)-toluene-4-sulfinyl)-but-2-enyl ester (172376-24-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) LDA / 1.) THF, -78 deg C, 10 min, 2.) -78 deg C, 1.5 h

2: 82 percent / pyridine / 3 h / 0 deg C -> room temperature

With pyridine; lithium diisopropyl amide;

DOI:10.1021/jo951264k

upstream raw materials:

(+)-(22R,23E,R_S)-22-hydroxy-6β-methoxy-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-26,27-dinorcholest-23-ene

Methanesulfonic anhydride

(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde

(R,E)-1-methyl-4-(prop-1-en-1-ylsulfinyl)benzene

Downstream raw materials:

(-)-(22Z,24R,R_S)-6β-methoxy-24-methyl-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-ergost-22-ene

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