(2R,8S,9S,10R,13S,14S,17S)-tert-butyl 2-benzyl-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

Base Information

Chemical Name:(2R,8S,9S,10R,13S,14S,17S)-tert-butyl 2-benzyl-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
CAS No.:1402153-83-6
Molecular Formula:C₃₁H₄₂O₃
Molecular Weight:462.673
Hs Code.:

(2R,8S,9S,10R,13S,14S,17S)-tert-butyl 2-benzyl-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

Synonyms:(2R,8S,9S,10R,13S,14S,17S)-tert-butyl 2-benzyl-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

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Chemical Property of (2R,8S,9S,10R,13S,14S,17S)-tert-butyl 2-benzyl-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

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Technology Process of (2R,8S,9S,10R,13S,14S,17S)-tert-butyl 2-benzyl-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

There total 6 articles about (2R,8S,9S,10R,13S,14S,17S)-tert-butyl 2-benzyl-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 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

: 1402154-18-0
(2S,8S,9S,10R,13S,14S,17S)-tert-butyl 2-benzyl-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

: 1402153-83-6
(2R,8S,9S,10R,13S,14S,17S)-tert-butyl 2-benzyl-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

Guidance literature:: Multi-step reaction with 2 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 - 0 °C / Inert atmosphere

With sulfuric acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
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

: 100-39-0
benzyl bromide

: 1402154-18-0
(2S,8S,9S,10R,13S,14S,17S)-tert-butyl 2-benzyl-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

: 1402153-83-6
(2R,8S,9S,10R,13S,14S,17S)-tert-butyl 2-benzyl-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

Guidance literature:: (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; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; at -78 - 0 ℃; for 3h; optical yield given as %de; Inert atmosphere;
DOI:10.1002/ejoc.201200190

Reference yield:

: 145-13-1
Pregnenolone

: 1402154-18-0
(2S,8S,9S,10R,13S,14S,17S)-tert-butyl 2-benzyl-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

: 1402153-83-6
(2R,8S,9S,10R,13S,14S,17S)-tert-butyl 2-benzyl-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

Guidance literature:: Multi-step reaction with 6 steps

1.1: iodine / 1.5 h / 90 °C / Inert atmosphere; Reflux

2.1: sodium methylate / 16 h / Inert atmosphere; Reflux

3.1: cyclohexanone; aluminum isopropoxide / toluene / 4 h / Reflux; Inert atmosphere

4.1: potassium hydroxide / methanol; water / 3 h / Inert atmosphere; Reflux

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

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

6.2: Inert atmosphere

6.3: 3 h / -78 - 0 °C / Inert atmosphere

With sulfuric acid; iodine; sodium methylate; cyclohexanone; aluminum isopropoxide; potassium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; toluene;
DOI:10.1002/ejoc.201200190