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

Base Information

• Chemical Name: (1S,2R,3R,4R,S_S)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-phenylbicyclo<2.2.1>hept-5-ene
• CAS No.: 177547-58-9
• Molecular Formula: C₂₅H₂₂O₃S
• Molecular Weight: 402.514

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

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

Chemical Property:

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

There total 7 articles about (1S,2R,3R,4R,S_S)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-phenylbicyclo<2.2.1>hept-5-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:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + (SS)-trans-2-Cinnamoyl-3-(tolyl-p-sulfinyl)furan (177547-56-7) → ((1R,2R,3R,4S)-3-Phenyl-bicyclo[2.2.1]hept-5-en-2-yl)-[3-((S)-toluene-4-sulfinyl)-furan-2-yl]-methanone + (1S,2R,3R,4R,SS)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-phenylbicyclo<2.2.1>hept-5-ene (177547-58-9) + ((1R,2S,3S,4S)-3-Phenyl-bicyclo[2.2.1]hept-5-en-2-yl)-[3-((S)-toluene-4-sulfinyl)-furan-2-yl]-methanone

Guidance literature:

With aluminium trichloride; In dichloromethane; at -20 ℃; for 3h; Yield given. Yields of byproduct given;

DOI:10.1039/P19960000759

Reference yield:

(1R/1S,SS)-1-<3-(p-tolylsulfinyl)-2-furyl>-trans-cinnamyl alcohol (211931-20-3) → (1S,2R,3R,4R,SS)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-phenylbicyclo<2.2.1>hept-5-ene (177547-58-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / MnO₂ / CHCl₃ / 0.5 h / Ambient temperature

2: AlCl₃ / CH₂Cl₂ / 3 h / -20 °C

With manganese(IV) oxide; aluminium trichloride; In dichloromethane; chloroform;

DOI:10.1039/P19960000759 DOI:10.1248/cpb.46.1078

Reference yield:

(E)-3-phenylpropenal (14371-10-9) → (1S,2R,3R,4R,SS)-2-<3-(p-tolylsulfinyl)-2-furoyl>-3-phenylbicyclo<2.2.1>hept-5-ene (177547-58-9)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 86 percent / MnO₂ / CHCl₃ / 0.5 h / Ambient temperature

3: AlCl₃ / CH₂Cl₂ / 3 h / -20 °C

With manganese(IV) oxide; aluminium trichloride; lithium diisopropyl amide; In dichloromethane; chloroform;

DOI:10.1248/cpb.46.1078

upstream raw materials:

cyclopenta-1,3-diene

(S_S)-trans-2-Cinnamoyl-3-(tolyl-p-sulfinyl)furan

(E)-3-phenylpropenal

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

Downstream raw materials:

(1R)-3-exo-Phenylbicyclo<2.2.1>heptane-2-endo-carboxylic acid

(1R,2R,3R,S_S)-2-<3'-(Tolyl-p-sulfinyl)-2'-furoyl>-3-phenylbicyclo<2.2.1>hept-5-ene

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