(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

Base Information

Chemical Name:(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
CAS No.:100467-45-6
Molecular Formula:C₂₅H₃₂O₇S
Molecular Weight:476.591
Hs Code.:

Synonyms:(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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Chemical Property of (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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Technology Process of (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

There total 13 articles about (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 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:

: 90397-80-1
(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

: 100467-45-6
(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

Guidance literature:: With ozone; In methanol; dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/jo00356a030

Reference yield:

: 5111-67-1
1-methyl-6-methoxy-2-tetralone

: 100467-45-6
(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

Guidance literature:: Multi-step reaction with 10 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

10: ozone / CH₂Cl₂; methanol / 0.5 h / -78 °C

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; ozone; 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:

: 38820-34-7
2,3,4,4a,9,10-hexahydro-7-methoxy-1,4aβ-dimethyl-2-phenanthrone

: 100467-45-6
(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

Guidance literature:: Multi-step reaction with 9 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

9: ozone / CH₂Cl₂; methanol / 0.5 h / -78 °C

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; ozone; triethylamine; dicyclohexyl-carbodiimide; cesium fluoride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/jo00356a030