(1S,4R,4aR,5R,8S,9aS)-4a-((S)-Toluene-4-sulfinyl)-1,4,4a,5,8,9a-hexahydro-1,4;5,8-dimethano-anthraquinone

Base Information

Chemical Name:(1S,4R,4aR,5R,8S,9aS)-4a-((S)-Toluene-4-sulfinyl)-1,4,4a,5,8,9a-hexahydro-1,4;5,8-dimethano-anthraquinone
CAS No.:187592-89-8
Molecular Formula:C₂₃H₂₀O₃S
Molecular Weight:376.476
Hs Code.:

Synonyms:(1S,4R,4aR,5R,8S,9aS)-4a-((S)-Toluene-4-sulfinyl)-1,4,4a,5,8,9a-hexahydro-1,4;5,8-dimethano-anthraquinone

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Chemical Property of (1S,4R,4aR,5R,8S,9aS)-4a-((S)-Toluene-4-sulfinyl)-1,4,4a,5,8,9a-hexahydro-1,4;5,8-dimethano-anthraquinone

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Technology Process of (1S,4R,4aR,5R,8S,9aS)-4a-((S)-Toluene-4-sulfinyl)-1,4,4a,5,8,9a-hexahydro-1,4;5,8-dimethano-anthraquinone

There total 3 articles about (1S,4R,4aR,5R,8S,9aS)-4a-((S)-Toluene-4-sulfinyl)-1,4,4a,5,8,9a-hexahydro-1,4;5,8-dimethano-anthraquinone 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: 79.0%

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: 161953-70-4
(5S,8R,SS)-5,8-methano-2-p-tolylsulfinyl-5,8-dihydro-1,4-naphthoquinone

: 187592-89-8
(1S,4R,4aR,5R,8S,9aS)-4a-((S)-Toluene-4-sulfinyl)-1,4,4a,5,8,9a-hexahydro-1,4;5,8-dimethano-anthraquinone

Guidance literature:: In dichloromethane; at -20 ℃; for 24h;
DOI:10.1021/jo9618942

Reference yield:

: 162060-46-0
endo-<4aR,5S,8R,8aS,(S)S>-5,8-methano-2-(p-tolylsulfinyl)-4a,5,8,8a-tetrahydro-1,4-naphthoquinone

: 187592-89-8
(1S,4R,4aR,5R,8S,9aS)-4a-((S)-Toluene-4-sulfinyl)-1,4,4a,5,8,9a-hexahydro-1,4;5,8-dimethano-anthraquinone

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / K₂CO₃ / tetrahydrofuran; H₂O / 1 h / Ambient temperature

2: 92 percent / aq. ceric ammonium nitrate / acetonitrile / 2 h / Ambient temperature

3: 79 percent / CH₂Cl₂ / 24 h / -20 °C

With ammonium cerium(IV) nitrate; potassium carbonate; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/jo9618942

Reference yield:

: 187592-86-5
(1S,4R)-6-((S)-Toluene-4-sulfinyl)-1,4-dihydro-1,4-methano-naphthalene-5,8-diol

: 187592-89-8
(1S,4R,4aR,5R,8S,9aS)-4a-((S)-Toluene-4-sulfinyl)-1,4,4a,5,8,9a-hexahydro-1,4;5,8-dimethano-anthraquinone

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / aq. ceric ammonium nitrate / acetonitrile / 2 h / Ambient temperature

2: 79 percent / CH₂Cl₂ / 24 h / -20 °C

With ammonium cerium(IV) nitrate; In dichloromethane; acetonitrile;
DOI:10.1021/jo9618942