(4aR,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-10-methoxy-9,12a-dimethyl-3-trimethylsilanyloxy-1,7a,8,8a,9,10,11,12,12a,12b-decahydro-2H-7-oxa-cyclopenta[k]phenanthren-6-one

Base Information

• Chemical Name: (4aR,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-10-methoxy-9,12a-dimethyl-3-trimethylsilanyloxy-1,7a,8,8a,9,10,11,12,12a,12b-decahydro-2H-7-oxa-cyclopenta[k]phenanthren-6-one
• CAS No.: 90397-80-1
• Molecular Formula: C₂₈H₄₀O₆SSi
• Molecular Weight: 532.774

Synonyms:(4aR,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-10-methoxy-9,12a-dimethyl-3-trimethylsilanyloxy-1,7a,8,8a,9,10,11,12,12a,12b-decahydro-2H-7-oxa-cyclopenta[k]phenanthren-6-one

Chemical Property of (4aR,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-10-methoxy-9,12a-dimethyl-3-trimethylsilanyloxy-1,7a,8,8a,9,10,11,12,12a,12b-decahydro-2H-7-oxa-cyclopenta[k]phenanthren-6-one

Chemical Property:

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Useful:

Technology Process of (4aR,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-10-methoxy-9,12a-dimethyl-3-trimethylsilanyloxy-1,7a,8,8a,9,10,11,12,12a,12b-decahydro-2H-7-oxa-cyclopenta[k]phenanthren-6-one

There total 11 articles about (4aR,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-10-methoxy-9,12a-dimethyl-3-trimethylsilanyloxy-1,7a,8,8a,9,10,11,12,12a,12b-decahydro-2H-7-oxa-cyclopenta[k]phenanthren-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:

1-methyl-6-methoxy-2-tetralone (5111-67-1) → (4aR,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-10-methoxy-9,12a-dimethyl-3-trimethylsilanyloxy-1,7a,8,8a,9,10,11,12,12a,12b-decahydro-2H-7-oxa-cyclopenta[k]phenanthren-6-one (90397-80-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 82 percent / K₂CO₃ / methanol / 48 h / Ambient temperature

2: 59 percent / lithium, ammonia / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating

3: 1.) sodium hydride / 1.) THF, reflux, 1 h, 2.) THF, reflux, 1 h

4: 89 percent / pyridine, p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

5: 94 percent / NaHCO₃, oxone / tetrahydrofuran; dioxane; H₂O / 1 h / Ambient temperature

6: 1.) LDA, 2.) N-chlorosuccinimide / 1.) THF, -78 deg C, 0.5 h, 2.) THF, -78 deg C, 0.5 h

7: 95 percent / N,N'-dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 2 h / Ambient temperature

8: 91 percent / cesium fluoride / CH₂Cl₂ / 26 h / Ambient temperature

9: 1.) cuprous iodide, methyllithium, 2.) HMPA, triethylamine / 1.) ethyl ether, THF, 0 deg C, 0.5 h, 2.) ethyl ether, THF, RT, 0.5 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; Oxone; N-chloro-succinimide; copper(l) iodide; ammonia; methyllithium; lithium; sodium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; cesium fluoride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo00356a030

Reference yield:

2,3,4,4a,9,10-hexahydro-7-methoxy-1,4aβ-dimethyl-2-phenanthrone (38820-34-7) → (4aR,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-10-methoxy-9,12a-dimethyl-3-trimethylsilanyloxy-1,7a,8,8a,9,10,11,12,12a,12b-decahydro-2H-7-oxa-cyclopenta[k]phenanthren-6-one (90397-80-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 59 percent / lithium, ammonia / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating

2: 1.) sodium hydride / 1.) THF, reflux, 1 h, 2.) THF, reflux, 1 h

3: 89 percent / pyridine, p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

4: 94 percent / NaHCO₃, oxone / tetrahydrofuran; dioxane; H₂O / 1 h / Ambient temperature

5: 1.) LDA, 2.) N-chlorosuccinimide / 1.) THF, -78 deg C, 0.5 h, 2.) THF, -78 deg C, 0.5 h

6: 95 percent / N,N'-dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 2 h / Ambient temperature

7: 91 percent / cesium fluoride / CH₂Cl₂ / 26 h / Ambient temperature

8: 1.) cuprous iodide, methyllithium, 2.) HMPA, triethylamine / 1.) ethyl ether, THF, 0 deg C, 0.5 h, 2.) ethyl ether, THF, RT, 0.5 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; Oxone; N-chloro-succinimide; copper(l) iodide; ammonia; methyllithium; lithium; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; cesium fluoride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo00356a030

Reference yield:

6-methoxy-2-tetralone (2472-22-2) → (4aR,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-10-methoxy-9,12a-dimethyl-3-trimethylsilanyloxy-1,7a,8,8a,9,10,11,12,12a,12b-decahydro-2H-7-oxa-cyclopenta[k]phenanthren-6-one (90397-80-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) pyrrolidine, p-toluenesulfonic acid / 1.) toluene, reflux, 18 h, 2.) a) methanol, RT, 1 h, b) reflux, 18 h

2: 82 percent / K₂CO₃ / methanol / 48 h / Ambient temperature

3: 59 percent / lithium, ammonia / tetrahydrofuran; 2-methyl-propan-2-ol / 2 h / Heating

4: 1.) sodium hydride / 1.) THF, reflux, 1 h, 2.) THF, reflux, 1 h

5: 89 percent / pyridine, p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

6: 94 percent / NaHCO₃, oxone / tetrahydrofuran; dioxane; H₂O / 1 h / Ambient temperature

7: 1.) LDA, 2.) N-chlorosuccinimide / 1.) THF, -78 deg C, 0.5 h, 2.) THF, -78 deg C, 0.5 h

8: 95 percent / N,N'-dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 2 h / Ambient temperature

9: 91 percent / cesium fluoride / CH₂Cl₂ / 26 h / Ambient temperature

10: 1.) cuprous iodide, methyllithium, 2.) HMPA, triethylamine / 1.) ethyl ether, THF, 0 deg C, 0.5 h, 2.) ethyl ether, THF, RT, 0.5 h

With pyrrolidine; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; Oxone; N-chloro-succinimide; copper(l) iodide; ammonia; methyllithium; lithium; sodium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; cesium fluoride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo00356a030

upstream raw materials:

1-methyl-6-methoxy-2-tetralone

2,3,4,4a,9,10-hexahydro-7-methoxy-1,4aβ-dimethyl-2-phenanthrone

6-methoxy-2-tetralone

1β,2α,3,4,4a,4bα,5,6,10,10aα-decahydro-7-methoxy-1α,4aβ-dimethyl-2β-phenanthrol methyl ether

Downstream raw materials:

(4R,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-3,4-dihydroxy-10-methoxy-9,12a-dimethyl-dodecahydro-7-oxa-cyclopenta[k]phenanthren-6-one

(3R,3aS,4R,4aS,7S,8S,8aS,9aR)-3-Benzenesulfonyl-7-methoxy-4a,8-dimethyl-2-oxo-4-(3-oxo-propyl)-decahydro-naphtho[2,3-b]furan-3a-carbaldehyde

(4R,5R,7aR,8aS,9S,10S,12aS,12bR)-5-Benzenesulfonyl-4-hydroxy-10-methoxy-9,12a-dimethyl-decahydro-7-oxa-cyclopenta[k]phenanthrene-3,6-dione

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