3β-(tert-butyldimethylsilyloxy)-22ξ-(phenylseleno)-14α,20ξ-card-5-enolide

Base Information

Chemical Name:3β-(tert-butyldimethylsilyloxy)-22ξ-(phenylseleno)-14α,20ξ-card-5-enolide
CAS No.:247067-76-1
Molecular Formula:C₃₅H₅₂O₃SeSi
Molecular Weight:627.842
Hs Code.:

Synonyms:3β-(tert-butyldimethylsilyloxy)-22ξ-(phenylseleno)-14α,20ξ-card-5-enolide

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 3β-(tert-butyldimethylsilyloxy)-22ξ-(phenylseleno)-14α,20ξ-card-5-enolide

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Technology Process of 3β-(tert-butyldimethylsilyloxy)-22ξ-(phenylseleno)-14α,20ξ-card-5-enolide

There total 7 articles about 3β-(tert-butyldimethylsilyloxy)-22ξ-(phenylseleno)-14α,20ξ-card-5-enolide 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: 75.0%

: 5707-04-0
Phenylselenyl chloride

: 247067-74-9
3β-(tert-butyldimethylsilyloxy)-14α,20ξ-card-5-enolide

: 247067-76-1
3β-(tert-butyldimethylsilyloxy)-22ξ-(phenylseleno)-14α,20ξ-card-5-enolide

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -70 ℃;
DOI:10.1016/S0040-4039(99)01130-2

Reference yield:

: Acetic acid (3S,8S,9S,10R,13S,14S,17S)-17-(1-methanesulfonyloxy-ethyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester

: 247067-76-1
3β-(tert-butyldimethylsilyloxy)-22ξ-(phenylseleno)-14α,20ξ-card-5-enolide

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium tert-butoxide / toluene / Heating

2.2: 82 percent / Zn / acetic acid / 2 h / 100 °C

3.1: 98 percent / K₂CO₃ / methanol / 4 h / 20 °C

4.1: 92 percent / imidazole / dimethylformamide / 1 h / 20 °C

5.1: 87 percent / NaOH; 30 percent H₂O₂ / methanol; tetrahydrofuran / 0.17 h / 20 °C

6.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 1 h / -30 - 0 °C

6.2: 75 percent / tetrahydrofuran; heptane; ethylbenzene / 3 h / -70 - -30 °C

With 1H-imidazole; sodium hydroxide; potassium tert-butylate; dihydrogen peroxide; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; n-heptane; ethylbenzene; N,N-dimethyl-formamide; toluene; 5.1: Baeyer-Villiger oxidation;
DOI:10.1002/ejoc.200400580

Reference yield:

: 72560-37-3
3-O-acetylpregna-5,20-dien-3β-ol

: 247067-76-1
3β-(tert-butyldimethylsilyloxy)-22ξ-(phenylseleno)-14α,20ξ-card-5-enolide

Guidance literature:: Multi-step reaction with 5 steps

1.2: 82 percent / Zn / acetic acid / 2 h / 100 °C

2.1: 98 percent / K₂CO₃ / methanol / 4 h / 20 °C

3.1: 92 percent / imidazole / dimethylformamide / 1 h / 20 °C

4.1: 87 percent / NaOH; 30 percent H₂O₂ / methanol; tetrahydrofuran / 0.17 h / 20 °C

5.1: lithium diisopropylamide / tetrahydrofuran; heptane; ethylbenzene / 1 h / -30 - 0 °C

5.2: 75 percent / tetrahydrofuran; heptane; ethylbenzene / 3 h / -70 - -30 °C

With 1H-imidazole; sodium hydroxide; dihydrogen peroxide; potassium carbonate; lithium diisopropyl amide; In tetrahydrofuran; methanol; n-heptane; ethylbenzene; N,N-dimethyl-formamide; 4.1: Baeyer-Villiger oxidation;
DOI:10.1002/ejoc.200400580