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

Base Information

Chemical Name:(20S)-1-[3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl]-2-propyn-1-ol
CAS No.:862259-65-2
Molecular Formula:C₃₈H₅₂O₂Si
Molecular Weight:568.915
Hs Code.:

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

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

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Technology Process of (20S)-1-[3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl]-2-propyn-1-ol

There total 7 articles about (20S)-1-[3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl]-2-propyn-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%

: 862259-62-9
(20S)-1-[3α-(tert-butyldiphenylsilyloxy)-5α-androstan-17β-yl]-3-triisopropylsilyl-2-propyn-1-ol

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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;
DOI:10.1021/jm050271q

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

With dmap; 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

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

Guidance literature:: Multi-step reaction with 4 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

With dmap; 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