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

Base Information

• Chemical Name: (R₁,S₂,S_S)-1-Benzyl 2-methyl 1-p-(tolylsulfinyl)-4-cyclohexene-1,2-dicarboxylate
• CAS No.: 155687-76-6
• Molecular Formula: C₂₃H₂₄O₅S
• Molecular Weight: 412.507

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

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

Chemical Property:

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

There total 1 articles about (R₁,S₂,S_S)-1-Benzyl 2-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:

buta-1,3-diene (106-99-0,130983-70-9,29406-96-0,9003-17-2) + (S)-1-Benzyl 4-methyl 2-p-tolylsulfinylmaleate (148871-72-1) → (R1,S2,SS)-1-Benzyl 2-methyl 1-p-(tolylsulfinyl)-4-cyclohexene-1,2-dicarboxylate (155687-76-6)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃; for 90h; regio- and stereoselectivity; other dienes; various catalysts and reaction conditions;

DOI:10.1021/jo00064a005

Reference yield:

(R1,S2,SS)-1-Benzyl 2-methyl 1-p-(tolylsulfinyl)-4-cyclohexene-1,2-dicarboxylate (155687-76-6) → (1S,2R)-2-(methoxycarbonyl)cyclohexanecarboxylic acid (88335-92-6)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 48 h / Ambient temperature

2: 95 percent / H₂ / PtO₂ / ethyl acetate / 24 h / 760 Torr / Ambient temperature

With hydrogen; platinum(IV) oxide; In dichloromethane; ethyl acetate;

DOI:10.1021/jo00085a043

Reference yield:

(R1,S2,SS)-1-Benzyl 2-methyl 1-p-(tolylsulfinyl)-4-cyclohexene-1,2-dicarboxylate (155687-76-6) → (1S,6R)-8-oxabicyclo[4.3.0]nonan-7-one (65376-02-5)

Guidance literature:

Multi-step reaction with 3 steps

1: CH₂Cl₂ / 48 h / Ambient temperature

2: 95 percent / H₂ / PtO₂ / ethyl acetate / 24 h / 760 Torr / Ambient temperature

3: 49 percent / BH₃*SMe₂ / tetrahydrofuran / 24 h / 0 °C

With dimethylsulfide borane complex; hydrogen; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/jo00085a043

upstream raw materials:

buta-1,3-diene

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

Downstream raw materials:

(1S,6R)-8-oxabicyclo[4.3.0]nonan-7-one

(1S,2R)-2-(methoxycarbonyl)cyclohexanecarboxylic acid

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