(20S)-1-{3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl-[3-(4-methoxyphenyl)-2-propynyl]}-1-ol

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Chemical Name:(20S)-1-{3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl-[3-(4-methoxyphenyl)-2-propynyl]}-1-ol
CAS No.:440368-49-0
Molecular Formula:C₄₅H₅₈O₃Si
Molecular Weight:675.039
Hs Code.:

Synonyms:(20S)-1-{3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl-[3-(4-methoxyphenyl)-2-propynyl]}-1-ol

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Chemical Property of (20S)-1-{3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl-[3-(4-methoxyphenyl)-2-propynyl]}-1-ol

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Technology Process of (20S)-1-{3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl-[3-(4-methoxyphenyl)-2-propynyl]}-1-ol

There total 8 articles about (20S)-1-{3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl-[3-(4-methoxyphenyl)-2-propynyl]}-1-ol 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: 84.0%

: 862259-65-2
(20S)-1-[3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl]-2-propyn-1-ol

: 696-62-8
para-iodoanisole

: 440368-49-0
(20S)-1-{3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl-[3-(4-methoxyphenyl)-2-propynyl]}-1-ol

Guidance literature:: With pyrrolidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; at 20 ℃; for 24h;
DOI:10.1021/jm050271q

Reference yield:

: 862259-67-4
3α-(tert-butyldiphenylsilyloxy)-5α-pregnan-20-one

: 440368-49-0
(20S)-1-{3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl-[3-(4-methoxyphenyl)-2-propynyl]}-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 97 percent / NaOBr / dioxane; H₂O / 24 h / 20 °C

2.1: 98 percent / EDCI; DMAP / CH₂Cl₂ / 2 h / 20 °C

3.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -40 °C

3.2: 70 percent / tetrahydrofuran; hexane / 2 h / -10 °C

4.1: 95 percent / (S)-3,3-diPh-1-Me-4hydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole; catecholborane / CH₂Cl₂; toluene / 5 h / -78 °C

5.1: 84 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

6.1: 84 percent / (PPh₃)4Pd; CuI; pyrrolidine / 24 h / 20 °C

With pyrrolidine; dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium hypobromide; tetrabutyl ammonium fluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; toluene;
DOI:10.1021/jm050271q

Reference yield:

: 862259-60-7
3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-carboxylic acid

: 440368-49-0
(20S)-1-{3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl-[3-(4-methoxyphenyl)-2-propynyl]}-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 98 percent / EDCI; DMAP / CH₂Cl₂ / 2 h / 20 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -40 °C

2.2: 70 percent / tetrahydrofuran; hexane / 2 h / -10 °C

3.1: 95 percent / (S)-3,3-diPh-1-Me-4hydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole; catecholborane / CH₂Cl₂; toluene / 5 h / -78 °C

4.1: 84 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

5.1: 84 percent / (PPh₃)4Pd; CuI; pyrrolidine / 24 h / 20 °C

With pyrrolidine; dmap; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tetrabutyl ammonium fluoride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1021/jm050271q