(R₁,S₂,S_S)-1-Benzyl 2-methyl 4-methyl-1-p-(tolylsulfinyl)-4-cyclohexene-1,2-dicarboxylate

Base Information

• Chemical Name: (R₁,S₂,S_S)-1-Benzyl 2-methyl 4-methyl-1-p-(tolylsulfinyl)-4-cyclohexene-1,2-dicarboxylate
• CAS No.: 155687-78-8
• Molecular Formula: C₂₄H₂₆O₅S
• Molecular Weight: 426.533

Synonyms:(R₁,S₂,S_S)-1-Benzyl 2-methyl 4-methyl-1-p-(tolylsulfinyl)-4-cyclohexene-1,2-dicarboxylate

Chemical Property of (R₁,S₂,S_S)-1-Benzyl 2-methyl 4-methyl-1-p-(tolylsulfinyl)-4-cyclohexene-1,2-dicarboxylate

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Technology Process of (R₁,S₂,S_S)-1-Benzyl 2-methyl 4-methyl-1-p-(tolylsulfinyl)-4-cyclohexene-1,2-dicarboxylate

There total 6 articles about (R₁,S₂,S_S)-1-Benzyl 2-methyl 4-methyl-1-p-(tolylsulfinyl)-4-cyclohexene-1,2-dicarboxylate 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:

(-)-menthyl p-toluenesulfinate (1517-82-4) → (R1,S2,SS)-1-Benzyl 2-methyl 4-methyl-1-p-(tolylsulfinyl)-4-cyclohexene-1,2-dicarboxylate (155687-78-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 67 percent / (i-Pr)2NMgBr / diethyl ether / 1 h / Ambient temperature

2: Et₃N, pyrrolidine / dimethylformamide; H₂O / 8 h / 0 °C

3: NaHCO₃, molecular sieves 4A / dimethylformamide / 4 h / Ambient temperature

4: TiCl₄ / CH₂Cl₂ / 28 h / -78 °C

With pyrrolidine; bromomagnesium diisopropylamide; 4 A molecular sieve; sodium hydrogencarbonate; triethylamine; titanium tetrachloride; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00085a043

Reference yield:

benzyl (R)-(+)-(p-tolylsulfinyl)acetate (148871-73-2) → (R1,S2,SS)-1-Benzyl 2-methyl 4-methyl-1-p-(tolylsulfinyl)-4-cyclohexene-1,2-dicarboxylate (155687-78-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N, pyrrolidine / dimethylformamide; H₂O / 8 h / 0 °C

2: NaHCO₃, molecular sieves 4A / dimethylformamide / 4 h / Ambient temperature

3: TiCl₄ / CH₂Cl₂ / 28 h / -78 °C

With pyrrolidine; 4 A molecular sieve; sodium hydrogencarbonate; triethylamine; titanium tetrachloride; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00085a043

Reference yield:

(S)-1-Benzyl 4-methyl 2-p-tolylsulfinylmaleate (148871-72-1) + isoprene (78-79-5,9003-31-0) → (R1,S2,SS)-1-Benzyl 2-methyl 4-methyl-1-p-(tolylsulfinyl)-4-cyclohexene-1,2-dicarboxylate (155687-78-8)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃; for 28h;

DOI:10.1021/jo00064a005

upstream raw materials:

(S)-1-Benzyl 4-methyl 2-p-tolylsulfinylmaleate

isoprene

Benzyl acetate

(-)-menthyl p-toluenesulfinate

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