3-benzyloxy-16-(2',2'-dibromoethenyl)-17-(thien-2''-yl)-estra-1,3,5⁽¹⁰⁾,16-tetraene

Base Information

• Chemical Name: 3-benzyloxy-16-(2',2'-dibromoethenyl)-17-(thien-2''-yl)-estra-1,3,5⁽¹⁰⁾,16-tetraene
• CAS No.: 897664-70-9
• Molecular Formula: C₃₁H₃₀Br₂OS
• Molecular Weight: 610.453

Synonyms:3-benzyloxy-16-(2',2'-dibromoethenyl)-17-(thien-2''-yl)-estra-1,3,5⁽¹⁰⁾,16-tetraene

Chemical Property of 3-benzyloxy-16-(2',2'-dibromoethenyl)-17-(thien-2''-yl)-estra-1,3,5⁽¹⁰⁾,16-tetraene

Chemical Property:

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Technology Process of 3-benzyloxy-16-(2',2'-dibromoethenyl)-17-(thien-2''-yl)-estra-1,3,5⁽¹⁰⁾,16-tetraene

There total 3 articles about 3-benzyloxy-16-(2',2'-dibromoethenyl)-17-(thien-2''-yl)-estra-1,3,5⁽¹⁰⁾,16-tetraene 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: 70.0%

3-benzyloxy-16-formyl-17-(2-thienyl)-estra-1,3,5(10),16-tetraene (897664-63-0) + carbon tetrabromide (558-13-4) → 3-benzyloxy-16-(2',2'-dibromoethenyl)-17-(thien-2''-yl)-estra-1,3,5(10),16-tetraene (897664-70-9)

Guidance literature:

With triphenylphosphine; In dichloromethane; at 20 ℃; for 17h;

DOI:10.1016/j.steroids.2005.06.001

Reference yield:

3-benzyloxy-16-tert-butoxymethylene-estra-1,3,5(10)-trien-1-7-one (897664-60-7) → 3-benzyloxy-16-(2',2'-dibromoethenyl)-17-(thien-2''-yl)-estra-1,3,5(10),16-tetraene (897664-70-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / pentane; diethyl ether / 1.5 h / -78 - 0 °C

1.2: diethyl ether; tetrahydrofuran; pentane / 5 h / 0 °C

1.3: 82 percent / p-tolueneusulfonic acid; water / diethyl ether; tetrahydrofuran; pentane / 25 h

2.1: 70 percent / PPh₃ / CH₂Cl₂ / 17 h / 20 °C

With n-butyllithium; triphenylphosphine; In diethyl ether; dichloromethane; pentane;

DOI:10.1016/j.steroids.2005.06.001

Reference yield:

16-hydroxymethylene-3-benzyloxyestra-1,3,5(10)-trien-17-one (444196-21-8) → 3-benzyloxy-16-(2',2'-dibromoethenyl)-17-(thien-2''-yl)-estra-1,3,5(10),16-tetraene (897664-70-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 81 percent / p-TsOH*H₂O / benzene / Heating

2.1: n-butyllithium / pentane; diethyl ether / 1.5 h / -78 - 0 °C

2.2: diethyl ether; tetrahydrofuran; pentane / 5 h / 0 °C

2.3: 82 percent / p-tolueneusulfonic acid; water / diethyl ether; tetrahydrofuran; pentane / 25 h

3.1: 70 percent / PPh₃ / CH₂Cl₂ / 17 h / 20 °C

With n-butyllithium; toluene-4-sulfonic acid; triphenylphosphine; In diethyl ether; dichloromethane; pentane; benzene;

DOI:10.1016/j.steroids.2005.06.001

upstream raw materials:

3-benzyloxy-16-formyl-17-(2-thienyl)-estra-1,3,5⁽¹⁰⁾,16-tetraene

carbon tetrabromide

3-benzyloxy-16-tert-butoxymethylene-estra-1,3,5⁽¹⁰⁾-trien-1-7-one

16-hydroxymethylene-3-benzyloxyestra-1,3,5⁽¹⁰⁾-trien-17-one

Downstream raw materials:

3-benzyloxy-16-ethynyl-17-(thien-2'-yl)-estra-1,3,5⁽¹⁰⁾,16-tetraene

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