(1R,2R,3R,4S,S_S)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-methylbicyclo<2.2.1>heptane

Base Information

• Chemical Name: (1R,2R,3R,4S,S_S)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-methylbicyclo<2.2.1>heptane
• CAS No.: 211931-26-9
• Molecular Formula: C₂₀H₂₂O₃S
• Molecular Weight: 342.459

Synonyms:(1R,2R,3R,4S,S_S)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-methylbicyclo<2.2.1>heptane

Chemical Property of (1R,2R,3R,4S,S_S)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-methylbicyclo<2.2.1>heptane

Chemical Property:

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Technology Process of (1R,2R,3R,4S,S_S)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-methylbicyclo<2.2.1>heptane

There total 4 articles about (1R,2R,3R,4S,S_S)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-methylbicyclo<2.2.1>heptane 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: 60.0%

(1S,2S,3R,4R,SS)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-methylbicyclo<2.2.1>hept-5-ene (177547-59-0) → (1R,2R,3R,4S,SS)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-methylbicyclo<2.2.1>heptane (211931-26-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2h; under 760 Torr;

DOI:10.1248/cpb.46.1078

Reference yield:

(+)-(SS)-3-(p-tolylsulfinyl)furan (143810-75-7) → (1R,2R,3R,4S,SS)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-methylbicyclo<2.2.1>heptane (211931-26-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 2.) THF, hexane

2: 73 percent / MnO₂ / CHCl₃ / 0.5 h / Ambient temperature

3: AlCl₃ / CH₂Cl₂ / 3 h / 25 °C

4: 60 percent / H₂ / 5 percent Pd/C / methanol / 2 h / 760 Torr

With manganese(IV) oxide; aluminium trichloride; hydrogen; lithium diisopropyl amide; palladium on activated charcoal; In methanol; dichloromethane; chloroform;

DOI:10.1248/cpb.46.1078

Reference yield:

(1R/1S,SS)-1-<3-(p-tolylsulfinyl)-2-furyl>-trans-crotyl alcohol (211931-21-4) → (1R,2R,3R,4S,SS)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-methylbicyclo<2.2.1>heptane (211931-26-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 73 percent / MnO₂ / CHCl₃ / 0.5 h / Ambient temperature

2: AlCl₃ / CH₂Cl₂ / 3 h / 25 °C

3: 60 percent / H₂ / 5 percent Pd/C / methanol / 2 h / 760 Torr

With manganese(IV) oxide; aluminium trichloride; hydrogen; palladium on activated charcoal; In methanol; dichloromethane; chloroform;

DOI:10.1248/cpb.46.1078

upstream raw materials:

(1S,2S,3R,4R,S_S)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-methylbicyclo<2.2.1>hept-5-ene

(+)-(SS)-3-(p-tolylsulfinyl)furan

(S_S)-2-trans-crotonyl-3-(p-tolylsulfinyl)furan

(1R/1S,S_S)-1-<3-(p-tolylsulfinyl)-2-furyl>-trans-crotyl alcohol

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