5-[3-(2-Ethoxy-ethoxy)-4-trimethylsilanylethynyl-phenyl]-pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-3-ethoxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Base Information

• Chemical Name: 5-[3-(2-Ethoxy-ethoxy)-4-trimethylsilanylethynyl-phenyl]-pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-3-ethoxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
• CAS No.: 220630-06-8
• Molecular Formula: C₄₁H₅₆O₅Si
• Molecular Weight: 656.978

Synonyms:5-[3-(2-Ethoxy-ethoxy)-4-trimethylsilanylethynyl-phenyl]-pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-3-ethoxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Chemical Property of 5-[3-(2-Ethoxy-ethoxy)-4-trimethylsilanylethynyl-phenyl]-pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-3-ethoxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Chemical Property:

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Technology Process of 5-[3-(2-Ethoxy-ethoxy)-4-trimethylsilanylethynyl-phenyl]-pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-3-ethoxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

There total 8 articles about 5-[3-(2-Ethoxy-ethoxy)-4-trimethylsilanylethynyl-phenyl]-pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-3-ethoxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 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:

testosterone (58-22-0) → 5-[3-(2-Ethoxy-ethoxy)-4-trimethylsilanylethynyl-phenyl]-pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-3-ethoxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (220630-06-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / DCC, DMAP / CH₂Cl₂ / 20 °C

2: 100 percent / TosOH / ethanol / 1 h / 20 °C

3: CuI, pyrrolidine / 2(PPh₃)2> / 20 °C

With pyrrolidine; dmap; copper(l) iodide; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; bis-triphenylphosphine-palladium(II) chloride; In ethanol; dichloromethane;

DOI:10.1002/(SICI)1521-3773(19981204)37:22<3154::AID-ANIE3154>3.0.CO;2-W

Reference yield:

N-(4-acetyl-3-hydroxyphenyl)acetamide (40547-58-8) → 5-[3-(2-Ethoxy-ethoxy)-4-trimethylsilanylethynyl-phenyl]-pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-3-ethoxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (220630-06-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 75 percent / K₂CO₃ / dimethylformamide / 5 h / 20 °C

2: 81 percent / HCl, H₂O / 100 °C

3: 1.) NaNO₂ / 1.) H₂O, 0 deg C, 15 min, 2.) H₂O, 0 deg C, 15 min

5: 78 percent / MeI / 17 h / 130 °C

6: CuI, pyrrolidine / 2(PPh₃)2> / 20 °C

With pyrrolidine; hydrogenchloride; copper(l) iodide; water; potassium carbonate; sodium nitrite; methyl iodide; bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide;

DOI:10.1002/(SICI)1521-3773(19981204)37:22<3154::AID-ANIE3154>3.0.CO;2-W

Reference yield:

Pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (220630-04-6) → 5-[3-(2-Ethoxy-ethoxy)-4-trimethylsilanylethynyl-phenyl]-pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-3-ethoxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (220630-06-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / TosOH / ethanol / 1 h / 20 °C

2: CuI, pyrrolidine / 2(PPh₃)2> / 20 °C

With pyrrolidine; copper(l) iodide; toluene-4-sulfonic acid; bis-triphenylphosphine-palladium(II) chloride; In ethanol;

DOI:10.1002/(SICI)1521-3773(19981204)37:22<3154::AID-ANIE3154>3.0.CO;2-W

upstream raw materials:

[2-(2-ethoxy-ethoxy)-4-iodo-phenylethynyl]-trimethyl-silane

Pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-3-ethoxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

testosterone

N-(4-acetyl-3-hydroxyphenyl)acetamide

Downstream raw materials:

5-[3-(2-Ethoxy-ethoxy)-4-ethynyl-phenyl]-pent-4-ynoic acid (8R,9S,10R,13S,14S,17S)-3-ethoxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

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