3,17β-Bis(benzyloxy)estra-11α-<(trimethylsilyl)ethynyl>estra-1,3,5(10)-trien-11β-ol

Base Information

Chemical Name:3,17β-Bis(benzyloxy)estra-11α-<(trimethylsilyl)ethynyl>estra-1,3,5(10)-trien-11β-ol
CAS No.:166183-94-4
Molecular Formula:C₃₇H₄₄O₃Si
Molecular Weight:564.84
Hs Code.:

Synonyms:3,17β-Bis(benzyloxy)estra-11α-<(trimethylsilyl)ethynyl>estra-1,3,5(10)-trien-11β-ol

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Chemical Property of 3,17β-Bis(benzyloxy)estra-11α-<(trimethylsilyl)ethynyl>estra-1,3,5(10)-trien-11β-ol

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Technology Process of 3,17β-Bis(benzyloxy)estra-11α-<(trimethylsilyl)ethynyl>estra-1,3,5(10)-trien-11β-ol

There total 4 articles about 3,17β-Bis(benzyloxy)estra-11α-<(trimethylsilyl)ethynyl>estra-1,3,5(10)-trien-11β-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: 85.0%

: 89155-71-5
(8S,9S,13S,14S,17S)-3,17-bis(benzyloxy)-13-methyl-6,7,8,9,12,13,14,15,16,17-decahydro-11H-cyclopenta[a]phenanthren-11-one

: 1066-54-2
trimethylsilylacetylene

: 166183-94-4
3,17β-Bis(benzyloxy)estra-11α-<(trimethylsilyl)ethynyl>estra-1,3,5(10)-trien-11β-ol

Guidance literature:: With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; 1.) 20 min, 2.) r.t., 1.5 h;
DOI:10.1021/jo00121a061

Reference yield:

: 1089-80-1
3-hydroxy-estra-1,3,5⁽¹⁰⁾,9⁽¹¹⁾-tetraen-17-one

: 166183-94-4
3,17β-Bis(benzyloxy)estra-11α-<(trimethylsilyl)ethynyl>estra-1,3,5(10)-trien-11β-ol

Guidance literature:: Multi-step reaction with 5 steps

1: NaBH₄ / methanol / 2 h / Ambient temperature

2: NaH / dimethylformamide; tetrahydrofuran / 18 h

3: 1.) catechol borane, LiBH₄, 2.) 33percent NaOH, 32percent aq. H₂O₂ / 1.) THF, 18 h, 2.) EtOH, r.t., 6 h

4: 57 percent / pyridinium chlorochromate / CH₂Cl₂ / 18 h

5: 85 percent / BuLi, diisopropylamine / hexane; tetrahydrofuran / 1.) 20 min, 2.) r.t., 1.5 h

With sodium hydroxide; sodium tetrahydroborate; lithium borohydride; n-butyllithium; dihydrogen peroxide; sodium hydride; diisopropylamine; pyridinium chlorochromate; benzo[1,3,2]dioxaborole; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00121a061

Reference yield:

: 791-69-5
9⁽¹¹⁾-Dehydroestradiol

: 166183-94-4
3,17β-Bis(benzyloxy)estra-11α-<(trimethylsilyl)ethynyl>estra-1,3,5(10)-trien-11β-ol

Guidance literature:: Multi-step reaction with 4 steps

1: NaH / dimethylformamide; tetrahydrofuran / 18 h

2: 1.) catechol borane, LiBH₄, 2.) 33percent NaOH, 32percent aq. H₂O₂ / 1.) THF, 18 h, 2.) EtOH, r.t., 6 h

3: 57 percent / pyridinium chlorochromate / CH₂Cl₂ / 18 h

4: 85 percent / BuLi, diisopropylamine / hexane; tetrahydrofuran / 1.) 20 min, 2.) r.t., 1.5 h

With sodium hydroxide; lithium borohydride; n-butyllithium; dihydrogen peroxide; sodium hydride; diisopropylamine; pyridinium chlorochromate; benzo[1,3,2]dioxaborole; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00121a061