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

Base Information

• Chemical Name: (-)-(22Z,24S,R_S)-6β-methoxy-24-methyl-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-ergost-22-ene
• CAS No.: 172376-21-5
• Molecular Formula: C₃₆H₅₄O₂S
• Molecular Weight: 550.89

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

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

Chemical Property:

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

There total 10 articles about (-)-(22Z,24S,R_S)-6β-methoxy-24-methyl-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-ergost-22-ene 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: 76.0%

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]-4-methyl-2-((S)-toluene-4-sulfinyl)-pent-2-enyl ester (172376-29-3) → (-)-(22Z,24S,RS)-6β-methoxy-24-methyl-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-ergost-22-ene (172376-21-5)

Guidance literature:

In tetrahydrofuran; at -23 - 0 ℃; for 2h;

DOI:10.1021/jo951264k

Reference yield: 76.0%

lithium methyl(cyano)cuprate + 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]-4-methyl-2-((S)-toluene-4-sulfinyl)-pent-2-enyl ester (172376-29-3) → (-)-(22Z,24S,RS)-6β-methoxy-24-methyl-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-ergost-22-ene (172376-21-5)

Guidance literature:

In tetrahydrofuran; at -23 - 0 ℃; for 2h;

DOI:10.1021/jo951264k

Reference yield:

(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde (25819-77-6) → (-)-(22Z,24S,RS)-6β-methoxy-24-methyl-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-ergost-22-ene (172376-21-5)

Guidance literature:

Multi-step reaction with 3 steps

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

2: pyridine / 0 °C

3: tetrahydrofuran / -78 deg C -> room temperature

With pyridine; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo951264k

upstream raw materials:

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]-4-methyl-2-((S)-toluene-4-sulfinyl)-pent-2-enyl ester

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

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

E-(RS)-1-(p-tolylsulfinyl)-4-methyl-1-but-1-ene

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