(2R,8S,9S,10R,13S,14S,17S)-methyl 17-(4-hydroxybenzoyl)-2,10,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate

Base Information

Chemical Name:(2R,8S,9S,10R,13S,14S,17S)-methyl 17-(4-hydroxybenzoyl)-2,10,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate
CAS No.:1402154-11-3
Molecular Formula:C₂₉H₃₆O₄
Molecular Weight:448.602
Hs Code.:

(2R,8S,9S,10R,13S,14S,17S)-methyl 17-(4-hydroxybenzoyl)-2,10,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate

Synonyms:(2R,8S,9S,10R,13S,14S,17S)-methyl 17-(4-hydroxybenzoyl)-2,10,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate

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Chemical Property of (2R,8S,9S,10R,13S,14S,17S)-methyl 17-(4-hydroxybenzoyl)-2,10,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate

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Technology Process of (2R,8S,9S,10R,13S,14S,17S)-methyl 17-(4-hydroxybenzoyl)-2,10,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate

There total 14 articles about (2R,8S,9S,10R,13S,14S,17S)-methyl 17-(4-hydroxybenzoyl)-2,10,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate 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:

: 302-97-6
androst-4-en-3-one-17β-carboxylic acid

: 1402154-11-3
(2R,8S,9S,10R,13S,14S,17S)-methyl 17-(4-hydroxybenzoyl)-2,10,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: sulfuric acid / dichloromethane / 16 h / -78 - 25 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: Inert atmosphere

2.3: 3 h / -78 - 25 °C / Inert atmosphere

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / Reflux; Inert atmosphere

4.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 2 h / -20 - 0 °C / Inert atmosphere

5.1: Pd(OAC)2(PPh₃)2; triethylamine / N,N-dimethyl-formamide / 3 h / 40 °C / Inert atmosphere

6.1: triethylsilane; trifluoroacetic acid / dichloromethane / 3 h / 25 °C / Inert atmosphere

7.1: triphenylphosphine / toluene / 16 h / Inert atmosphere

8.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

8.2: 1 h / -50 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

With triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; sulfuric acid; Pd(OAC)2(PPh₃)2; tetrabutyl ammonium fluoride; isopropylmagnesium chloride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/ejoc.201200190

Reference yield:

: C₃₅H₅₀O₄Si

: 1402154-11-3
(2R,8S,9S,10R,13S,14S,17S)-methyl 17-(4-hydroxybenzoyl)-2,10,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;
DOI:10.1002/ejoc.201200190

Reference yield:

: 1402153-81-4
(8S,9S,10R,13S,14S,17S)-tert-butyl 10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate

: 1402154-11-3
(2R,8S,9S,10R,13S,14S,17S)-methyl 17-(4-hydroxybenzoyl)-2,10,13-trimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: Inert atmosphere

1.3: 3 h / -78 - 25 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 16 h / Reflux; Inert atmosphere

3.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 2 h / -20 - 0 °C / Inert atmosphere

4.1: Pd(OAC)2(PPh₃)2; triethylamine / N,N-dimethyl-formamide / 3 h / 40 °C / Inert atmosphere

5.1: triethylsilane; trifluoroacetic acid / dichloromethane / 3 h / 25 °C / Inert atmosphere

6.1: triphenylphosphine / toluene / 16 h / Inert atmosphere

7.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

7.2: 1 h / -50 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

With triethylsilane; 2,6-di-tert-butyl-4-methylpyridine; Pd(OAC)2(PPh₃)2; tetrabutyl ammonium fluoride; isopropylmagnesium chloride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/ejoc.201200190