(20S)-3β-(tert-butyldimethylsiloxy)-11α-(2-methoxyethoxymethoxy)-22-phenylsulfonyl-23,24-dinorchol-5-ene

Base Information

Chemical Name:(20S)-3β-(tert-butyldimethylsiloxy)-11α-(2-methoxyethoxymethoxy)-22-phenylsulfonyl-23,24-dinorchol-5-ene
CAS No.:156178-19-7
Molecular Formula:C₃₈H₆₂O₆SSi
Molecular Weight:675.058
Hs Code.:

Synonyms:(20S)-3β-(tert-butyldimethylsiloxy)-11α-(2-methoxyethoxymethoxy)-22-phenylsulfonyl-23,24-dinorchol-5-ene

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Chemical Property of (20S)-3β-(tert-butyldimethylsiloxy)-11α-(2-methoxyethoxymethoxy)-22-phenylsulfonyl-23,24-dinorchol-5-ene

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Technology Process of (20S)-3β-(tert-butyldimethylsiloxy)-11α-(2-methoxyethoxymethoxy)-22-phenylsulfonyl-23,24-dinorchol-5-ene

There total 7 articles about (20S)-3β-(tert-butyldimethylsiloxy)-11α-(2-methoxyethoxymethoxy)-22-phenylsulfonyl-23,24-dinorchol-5-ene 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: 97.0%

: 3970-21-6
2-Methoxyethoxymethyl chloride

: 156178-18-6
(20S)-3β-(tert-butyldimethylsiloxy)-22-phenylsulfonyl-23,24-dinorchol-5-en-11α-ol

: 156178-19-7
(20S)-3β-(tert-butyldimethylsiloxy)-11α-(2-methoxyethoxymethoxy)-22-phenylsulfonyl-23,24-dinorchol-5-ene

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 3h; Ambient temperature;
DOI:10.1039/P19940000269

Reference yield:

: 142886-19-9
<17(20)Z>-pregna-5,17(20)-diene-3β,11α-diyl diacetate

: 156178-19-7
(20S)-3β-(tert-butyldimethylsiloxy)-11α-(2-methoxyethoxymethoxy)-22-phenylsulfonyl-23,24-dinorchol-5-ene

Guidance literature:: Multi-step reaction with 7 steps

1: 83 percent / BF₃*OEt₂ / CH₂Cl₂ / 6 h / 0 °C

2: 98 percent / H₂ / Pt/C / ethyl acetate / 0.22 h / Ambient temperature

3: 93 percent / pyridine / 16 h / 4 °C

4: 1.) LiBr, Li₂CO₃ / 1) DMF, 85 deg C, 95 min; 2) DMF, 3 h, 85 deg C

5: 98 percent / aq. KOH / methanol; tetrahydrofuran / 2 h / 60 °C

6: 87 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature

7: 97 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; 1H-imidazole; potassium hydroxide; boron trifluoride diethyl etherate; hydrogen; lithium carbonate; N-ethyl-N,N-diisopropylamine; lithium bromide; platinum on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1039/P19940000269

Reference yield:

: 156178-13-1
(20S)-22-hydroxy-23,24-dinorchola-5,16-diene-3β,11α-diyl diacetate

: 156178-19-7
(20S)-3β-(tert-butyldimethylsiloxy)-11α-(2-methoxyethoxymethoxy)-22-phenylsulfonyl-23,24-dinorchol-5-ene

Guidance literature:: Multi-step reaction with 6 steps

1: 98 percent / H₂ / Pt/C / ethyl acetate / 0.22 h / Ambient temperature

2: 93 percent / pyridine / 16 h / 4 °C

3: 1.) LiBr, Li₂CO₃ / 1) DMF, 85 deg C, 95 min; 2) DMF, 3 h, 85 deg C

4: 98 percent / aq. KOH / methanol; tetrahydrofuran / 2 h / 60 °C

5: 87 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature

6: 97 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / Ambient temperature

With pyridine; 1H-imidazole; potassium hydroxide; hydrogen; lithium carbonate; N-ethyl-N,N-diisopropylamine; lithium bromide; platinum on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1039/P19940000269