(-)-(R_S)-(p-tolylsulfinyl)stigmasteryl isomethyl ether

Base Information

• Chemical Name: (-)-(R_S)-(p-tolylsulfinyl)stigmasteryl isomethyl ether
• CAS No.: 172376-34-0
• Molecular Formula: C₃₇H₅₆O₂S
• Molecular Weight: 564.916

Synonyms:

Chemical Property of (-)-(R_S)-(p-tolylsulfinyl)stigmasteryl isomethyl ether

Chemical Property:

Purity/Quality:

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Technology Process of (-)-(R_S)-(p-tolylsulfinyl)stigmasteryl isomethyl ether

There total 5 articles about (-)-(R_S)-(p-tolylsulfinyl)stigmasteryl isomethyl ether 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: 73.0%

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) → (-)-(RS)-(p-tolylsulfinyl)stigmasteryl isomethyl ether (172376-34-0)

Guidance literature:

In tetrahydrofuran; for 4h; -23 deg C -> room temperature;

DOI:10.1021/jo951264k

Reference yield:

(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde (25819-77-6) → (-)-(RS)-(p-tolylsulfinyl)stigmasteryl isomethyl ether (172376-34-0)

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

3: 73 percent / tetrahydrofuran / 4 h / -23 deg C -> room temperature

With pyridine; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jo951264k

Reference yield:

1-iodo-3-methyl-1-p-tolylsulfenyl-1-butene → (-)-(RS)-(p-tolylsulfinyl)stigmasteryl isomethyl ether (172376-34-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) t-BuLi / 1.) THF, 10 min, 2.) -78 deg C, 15 min

2: m-CPBA / CH₂Cl₂ / 0 °C

3: 84 percent / pyridine / 3 h / 0 deg C -> room temperature

4: 73 percent / tetrahydrofuran / 4 h / -23 deg C -> room temperature

With pyridine; tert.-butyl lithium; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

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

(+)-(22R,23E)-22-hydroxy-6β-methoxy-23-(p-tolylsulfenyl)-3α,5-cyclo-5α-cholest-23-ene

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

Downstream raw materials:

stigmasterol methyl ether

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