2-[4-(3-hydroxy-3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl)phenoxy]ethyl methanesulfonate

Base Information

Chemical Name:2-[4-(3-hydroxy-3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl)phenoxy]ethyl methanesulfonate
CAS No.:261718-48-3
Molecular Formula:C₂₇H₃₄O₆S
Molecular Weight:486.629
Hs Code.:

Synonyms:2-[4-(3-hydroxy-3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl)phenoxy]ethyl methanesulfonate

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Chemical Property of 2-[4-(3-hydroxy-3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl)phenoxy]ethyl methanesulfonate

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Technology Process of 2-[4-(3-hydroxy-3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl)phenoxy]ethyl methanesulfonate

There total 5 articles about 2-[4-(3-hydroxy-3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl)phenoxy]ethyl methanesulfonate 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: 88.0%

: 261718-46-1
2-[4-(3-hydroxy-17-oxoestra-1,3,5(10)-trien-11β-yl)phenoxy]ethyl methanesulfonate

: 261718-48-3
2-[4-(3-hydroxy-3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl)phenoxy]ethyl methanesulfonate

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; methanol; at 0 ℃; for 1h;
DOI:10.1021/jm990179s

Reference yield:

: 134414-14-5
11beta-(4-hydroxyphenyl)-estra-4,9-diene-3,17-dione

: 261718-48-3
2-[4-(3-hydroxy-3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl)phenoxy]ethyl methanesulfonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 0.42 h

1.2: dimethylformamide / 22 h / 20 °C

2.1: 57 percent / 6 N aq. HCl / dimethylformamide / 1 h / 20 °C

3.1: 98 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

4.1: AcBr; Ac₂O / CH₂Cl₂ / 1.5 h / 0 - 20 °C

4.2: 74 percent / 2 N aq. NaOH / methanol; tetrahydrofuran / 0.75 h / 20 °C

5.1: 88 percent / NaBH₄ / methanol; tetrahydrofuran / 1 h / 0 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; Acetyl bromide; acetic anhydride; sodium hydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: deprotonation / 1.2: Alkylation / 2.1: desilylation / 3.1: mesylation / 4.1: Aromatization / 4.2: Hydrolysis / 5.1: Reduction;
DOI:10.1021/jm990179s

Reference yield:

: 261718-44-9
11β-[4-(2-hydroxyethoxy)phenyl]estra-4,9-diene-3,17-dione

: 261718-48-3
2-[4-(3-hydroxy-3,17β-dihydroxyestra-1,3,5(10)-trien-11β-yl)phenoxy]ethyl methanesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 98 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 0 °C

2.1: AcBr; Ac₂O / CH₂Cl₂ / 1.5 h / 0 - 20 °C

2.2: 74 percent / 2 N aq. NaOH / methanol; tetrahydrofuran / 0.75 h / 20 °C

3.1: 88 percent / NaBH₄ / methanol; tetrahydrofuran / 1 h / 0 °C

With dmap; sodium tetrahydroborate; Acetyl bromide; acetic anhydride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1.1: mesylation / 2.1: Aromatization / 2.2: Hydrolysis / 3.1: Reduction;
DOI:10.1021/jm990179s