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

Base Information

• Chemical Name: (+)-(22R,23E,S_S)-22-hydroxy-6β-methoxy-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-cholest-23-ene
• CAS No.: 172376-25-9
• Molecular Formula: C₃₅H₅₂O₃S
• Molecular Weight: 552.862

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

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

Chemical Property:

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

There total 5 articles about (+)-(22R,23E,S_S)-22-hydroxy-6β-methoxy-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-cholest-23-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: 90.0%

(+)-(22R,23E)-22-hydroxy-6β-methoxy-23-(p-tolylsulfenyl)-3α,5-cyclo-5α-cholest-23-ene (172376-27-1) → (+)-(22R,23E,SS)-22-hydroxy-6β-methoxy-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-cholest-23-ene (172376-25-9)

Guidance literature:

With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; Cumene hydroperoxide; In dichloromethane; at -20 ℃; for 60h;

DOI:10.1021/jo951264k

Reference yield:

(+)-(22R,23E)-22-hydroxy-6β-methoxy-23-(p-tolylsulfenyl)-3α,5-cyclo-5α-cholest-23-ene (172376-27-1) → (+)-(22R,23E,SS)-22-hydroxy-6β-methoxy-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-cholest-23-ene (172376-25-9) + (+)-(22R,23E,RS)-22-hydroxy-6β-methoxy-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-cholest-23-ene (172376-20-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; Yield given. Yields of byproduct given;

DOI:10.1021/jo951264k

Reference yield:

(20S)-6β-methoxy-3α,5-cyclo-5α-pregnane-20-carbaldehyde (25819-77-6) → (+)-(22R,23E,SS)-22-hydroxy-6β-methoxy-23-(p-tolylsulfinyl)-3α,5-cyclo-5α-cholest-23-ene (172376-25-9)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 90 percent / Ti(OiPr)4, (L)-(+)-diethyl tartrate, cumene hydroperoxide / CH₂Cl₂ / 60 h / -20 °C

With titanium(IV) isopropylate; diethyl (2R,3R)-tartrate; Cumene hydroperoxide; tert.-butyl lithium; In dichloromethane;

DOI:10.1021/jo951264k

upstream raw materials:

(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

Downstream raw materials:

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

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-((R)-toluene-4-sulfinyl)-pent-2-enyl ester

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