Toluene-4-sulfonic acid 3-[(1R,5R)-1,2-dimethyl-5-((S)-1-methyl-2-oxo-ethyl)-cyclopent-2-enyl]-propyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid 3-[(1R,5R)-1,2-dimethyl-5-((S)-1-methyl-2-oxo-ethyl)-cyclopent-2-enyl]-propyl ester
CAS No.:96837-65-9
Molecular Formula:C₂₀H₂₈O₄S
Molecular Weight:364.506
Hs Code.:

Synonyms:Toluene-4-sulfonic acid 3-[(1R,5R)-1,2-dimethyl-5-((S)-1-methyl-2-oxo-ethyl)-cyclopent-2-enyl]-propyl ester

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Chemical Property of Toluene-4-sulfonic acid 3-[(1R,5R)-1,2-dimethyl-5-((S)-1-methyl-2-oxo-ethyl)-cyclopent-2-enyl]-propyl ester

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Technology Process of Toluene-4-sulfonic acid 3-[(1R,5R)-1,2-dimethyl-5-((S)-1-methyl-2-oxo-ethyl)-cyclopent-2-enyl]-propyl ester

There total 8 articles about Toluene-4-sulfonic acid 3-[(1R,5R)-1,2-dimethyl-5-((S)-1-methyl-2-oxo-ethyl)-cyclopent-2-enyl]-propyl ester 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: 82.0%

: 96837-64-8,96894-70-1
Toluene-4-sulfonic acid 3-((1R,3S,4R,7R)-2-hydroxy-1,3,7-trimethyl-bicyclo[2.2.1]hept-7-yl)-propyl ester

: 96837-65-9
Toluene-4-sulfonic acid 3-[(1R,5R)-1,2-dimethyl-5-((S)-1-methyl-2-oxo-ethyl)-cyclopent-2-enyl]-propyl ester

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; at 0 ℃; for 0.166667h;
DOI:10.1016/S0040-4020(01)83472-4

Reference yield:

: 10293-10-4
3-endo-9-dibromo-1,7,7-trimethylbicyclo<2.2.1>heptan-2-one

: 96837-65-9
Toluene-4-sulfonic acid 3-[(1R,5R)-1,2-dimethyl-5-((S)-1-methyl-2-oxo-ethyl)-cyclopent-2-enyl]-propyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: Zn / benzene; dimethylsulfoxide / 11 h / 60 °C

2: 1.) i-Pr₂NH, n-BuLi / 1.) hexane, THF, -78 deg C, 0.33 h; 2.) THF, -78 deg C to r.t.

3: Na / methanol / 24 h / Ambient temperature

4: 95.8 percent / KI / dimethylformamide / 12 h / 100 °C

5: 1.) KH; 3.) KI, water / 1.) ether, reflux, 2 h; 2.) DMF, 130 deg C, 24 h; 3.) DMF, 140 deg C, 24 h

6: 94.3 percent / LiAlH₄ / tetrahydrofuran / 24 h / Ambient temperature

7: 50 percent / pyridine / 48 h / 4 °C

8: 82 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.17 h / 0 °C

With pyridine; lithium aluminium tetrahydride; n-butyllithium; ammonium cerium(IV) nitrate; water; sodium; potassium hydride; diisopropylamine; potassium iodide; zinc; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1016/S0040-4020(01)83472-4

Reference yield:

: 10293-09-1
(1R,4R,7R)-9-bromocamphor

: 96837-65-9
Toluene-4-sulfonic acid 3-[(1R,5R)-1,2-dimethyl-5-((S)-1-methyl-2-oxo-ethyl)-cyclopent-2-enyl]-propyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) i-Pr₂NH, n-BuLi / 1.) hexane, THF, -78 deg C, 0.33 h; 2.) THF, -78 deg C to r.t.

2: Na / methanol / 24 h / Ambient temperature

3: 95.8 percent / KI / dimethylformamide / 12 h / 100 °C

4: 1.) KH; 3.) KI, water / 1.) ether, reflux, 2 h; 2.) DMF, 130 deg C, 24 h; 3.) DMF, 140 deg C, 24 h

5: 94.3 percent / LiAlH₄ / tetrahydrofuran / 24 h / Ambient temperature

6: 50 percent / pyridine / 48 h / 4 °C

7: 82 percent / ceric ammonium nitrate / acetonitrile; H₂O / 0.17 h / 0 °C

With pyridine; lithium aluminium tetrahydride; n-butyllithium; ammonium cerium(IV) nitrate; water; sodium; potassium hydride; diisopropylamine; potassium iodide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(01)83472-4