(1'S,3aS,4R,5S,6aR)-5-allyl-2-(1-benzenesulfonyl-hept-6-enyl)-4-isopropyl-1-(toluene-4-sulfonyl)-3a,4,5,6a-tetrahydro-1H-cyclopenta[b]pyrrol-6-one

Base Information

• Chemical Name: (1'S,3aS,4R,5S,6aR)-5-allyl-2-(1-benzenesulfonyl-hept-6-enyl)-4-isopropyl-1-(toluene-4-sulfonyl)-3a,4,5,6a-tetrahydro-1H-cyclopenta[b]pyrrol-6-one
• CAS No.: 275364-80-2
• Molecular Formula: C₃₃H₄₁NO₅S₂
• Molecular Weight: 595.824

Synonyms:(1'S,3aS,4R,5S,6aR)-5-allyl-2-(1-benzenesulfonyl-hept-6-enyl)-4-isopropyl-1-(toluene-4-sulfonyl)-3a,4,5,6a-tetrahydro-1H-cyclopenta[b]pyrrol-6-one

Chemical Property of (1'S,3aS,4R,5S,6aR)-5-allyl-2-(1-benzenesulfonyl-hept-6-enyl)-4-isopropyl-1-(toluene-4-sulfonyl)-3a,4,5,6a-tetrahydro-1H-cyclopenta[b]pyrrol-6-one

Chemical Property:

Purity/Quality:

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Technology Process of (1'S,3aS,4R,5S,6aR)-5-allyl-2-(1-benzenesulfonyl-hept-6-enyl)-4-isopropyl-1-(toluene-4-sulfonyl)-3a,4,5,6a-tetrahydro-1H-cyclopenta[b]pyrrol-6-one

There total 11 articles about (1'S,3aS,4R,5S,6aR)-5-allyl-2-(1-benzenesulfonyl-hept-6-enyl)-4-isopropyl-1-(toluene-4-sulfonyl)-3a,4,5,6a-tetrahydro-1H-cyclopenta[b]pyrrol-6-one 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: 52.0%

(1'S,3aR,4R,6aR)-2-(1-benzenesulfonyl-hept-6-enyl)-5-bromo-4-isopropyl-1-(toluene-4-sulfonyl)-3a,4,5,6a-tetrahydro-1H-cyclopenta[b]pyrrol-6-one (275364-90-4) + allyltributylstanane (24850-33-7) → (1'S,3aS,4R,5S,6aR)-5-allyl-2-(1-benzenesulfonyl-hept-6-enyl)-4-isopropyl-1-(toluene-4-sulfonyl)-3a,4,5,6a-tetrahydro-1H-cyclopenta[b]pyrrol-6-one (275364-80-2)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); In toluene; at 100 ℃; for 3h;

DOI:10.1021/ol005750s

Reference yield:

(3aR,6aR)-1-(Toluene-4-sulfonyl)-1,3,3a,6a-tetrahydro-cyclopenta[b]pyrrole-2,6-dione (201014-33-7) → (1'S,3aS,4R,5S,6aR)-5-allyl-2-(1-benzenesulfonyl-hept-6-enyl)-4-isopropyl-1-(toluene-4-sulfonyl)-3a,4,5,6a-tetrahydro-1H-cyclopenta[b]pyrrol-6-one (275364-80-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 83 percent / CuI; BF₃*Et₂O / tetrahydrofuran / -78 °C

2.1: 97 percent / p-toluenesulfonic acid / methanol / 2 h / 70 °C

3.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

3.2: hexamethylphosphoramide / tetrahydrofuran; toluene / 2 h / -78 - 0 °C

4.1: 71 percent / triphenylarsine; lithium chloride; triethylamine / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ / acetonitrile / 1 h / 50 °C / 15201 Torr

5.1: 78 percent / diisobutylaluminium hydride / tetrahydrofuran; toluene / 2 h / -78 - 0 °C

6.1: 96 percent / triphenylphosphine; imidazole; iodine / diethyl ether; acetonitrile / 1 h / 0 °C

7.1: 95 percent / hexamethylphosphoramide / dimethylformamide / 2 h / 45 °C

8.1: n-BuLi; hexamethylphosphoramide / tetrahydrofuran; various solvent(s) / -78 °C

8.2: 65 percent / tetrahydrofuran / 2 h / -78 - -40 °C

9.1: 99 percent / aq. HCl / acetone / 4 h / 50 °C

10.1: 92 percent / copper(II) bromide / ethyl acetate / 2 h / 50 °C

11.1: 52 percent / 2,2'-azobisisobutyronitrile / toluene / 3 h / 100 °C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; n-butyllithium; 2,2'-azobis(isobutyronitrile); triphenyl-arsane; boron trifluoride diethyl etherate; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; lithium chloride; copper(ll) bromide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1.1: Addition / 2.1: Etherification / 3.1: Addition / 3.2: Substitution / 4.1: Carbonylation / 5.1: Reduction / 6.1: Iodination / 7.1: Substitution / 8.1: Metallation / 8.2: Alkylation / 9.1: Hydrolysis / 10.1: Bromination / 11.1: Alkylation;

DOI:10.1021/ol005750s

Reference yield:

(3aR,4R,6aR)-4-Isopropyl-1-(toluene-4-sulfonyl)-hexahydro-cyclopenta[b]pyrrole-2,6-dione (201014-29-1) → (1'S,3aS,4R,5S,6aR)-5-allyl-2-(1-benzenesulfonyl-hept-6-enyl)-4-isopropyl-1-(toluene-4-sulfonyl)-3a,4,5,6a-tetrahydro-1H-cyclopenta[b]pyrrol-6-one (275364-80-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 97 percent / p-toluenesulfonic acid / methanol / 2 h / 70 °C

2.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

2.2: hexamethylphosphoramide / tetrahydrofuran; toluene / 2 h / -78 - 0 °C

3.1: 71 percent / triphenylarsine; lithium chloride; triethylamine / tris(dibenzylideneacetone)dipalladium⁽⁰⁾ / acetonitrile / 1 h / 50 °C / 15201 Torr

4.1: 78 percent / diisobutylaluminium hydride / tetrahydrofuran; toluene / 2 h / -78 - 0 °C

5.1: 96 percent / triphenylphosphine; imidazole; iodine / diethyl ether; acetonitrile / 1 h / 0 °C

6.1: 95 percent / hexamethylphosphoramide / dimethylformamide / 2 h / 45 °C

7.1: n-BuLi; hexamethylphosphoramide / tetrahydrofuran; various solvent(s) / -78 °C

7.2: 65 percent / tetrahydrofuran / 2 h / -78 - -40 °C

8.1: 99 percent / aq. HCl / acetone / 4 h / 50 °C

9.1: 92 percent / copper(II) bromide / ethyl acetate / 2 h / 50 °C

10.1: 52 percent / 2,2'-azobisisobutyronitrile / toluene / 3 h / 100 °C

With 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 2,2'-azobis(isobutyronitrile); triphenyl-arsane; iodine; potassium hexamethylsilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; lithium chloride; copper(ll) bromide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1.1: Etherification / 2.1: Addition / 2.2: Substitution / 3.1: Carbonylation / 4.1: Reduction / 5.1: Iodination / 6.1: Substitution / 7.1: Metallation / 7.2: Alkylation / 8.1: Hydrolysis / 9.1: Bromination / 10.1: Alkylation;

DOI:10.1021/ol005750s

upstream raw materials:

(1'S,3aR,4R,6aR)-2-(1-benzenesulfonyl-hept-6-enyl)-5-bromo-4-isopropyl-1-(toluene-4-sulfonyl)-3a,4,5,6a-tetrahydro-1H-cyclopenta[b]pyrrol-6-one

allyltributylstanane

(3aR,6aR)-1-(Toluene-4-sulfonyl)-1,3,3a,6a-tetrahydro-cyclopenta[b]pyrrole-2,6-dione

(3aR,4R,6aR)-4-Isopropyl-1-(toluene-4-sulfonyl)-hexahydro-cyclopenta[b]pyrrole-2,6-dione

Downstream raw materials:

(4S,12S,13S)-4-benzenesulfonyl-13-isopropyl-2-aza-tricyclo[10.2.1.1^3,14]-hexadeca-1⁽¹⁴⁾,3⁽¹⁶⁾,9-trien-15-one

(1R,4S,12S,13R,14S)-4-benzenesulfonyl-13-isopropyl-2-(toluene-4-sulfonyl)-2-azatricyclo[10.2.1.1^3,4]hexadeca-3⁽¹⁶⁾,9-dien-15-one

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