(R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-12-(4-pyridin-4-yl-benzyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester

Base Information

• Chemical Name: (R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-12-(4-pyridin-4-yl-benzyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester
• CAS No.: 219596-45-9
• Molecular Formula: C₃₇H₅₁NO₄
• Molecular Weight: 573.816

Synonyms:(R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-12-(4-pyridin-4-yl-benzyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester

Chemical Property of (R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-12-(4-pyridin-4-yl-benzyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester

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Technology Process of (R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-12-(4-pyridin-4-yl-benzyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester

There total 3 articles about (R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-12-(4-pyridin-4-yl-benzyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl 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: 70.0%

4-trimethylstannyl-pyridine (59020-06-3) + (R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-Acetoxy-12-(4-bromo-benzyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester → (R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-12-(4-pyridin-4-yl-benzyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester (219596-45-9)

Guidance literature:

4-trimethylstannyl-pyridine; (R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-Acetoxy-12-(4-bromo-benzyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; for 48h; Heating;

With potassium methanolate; In tetrahydrofuran; methanol; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(00)01866-9

Reference yield:

methyl 3α-acetoxy-12α-hydroxy-5β-cholan-24-oate (27240-83-1) → (R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-12-(4-pyridin-4-yl-benzyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester (219596-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 70 percent / F₃CSO₃H; 4 Angstroem mol. sieves / CCl₄; cyclohexane / 3 h / 20 °C

2.1: Pd(PPh₃)4 / toluene / 48 h / Heating

2.2: 70 percent / KOMe / methanol; tetrahydrofuran / 1 h / 20 °C

With trifluorormethanesulfonic acid; 4 A molecular sieve; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrachloromethane; cyclohexane; toluene; 2.1: Stille reaction;

DOI:10.1016/S0040-4039(00)01866-9

Reference yield:

(4-bromobenzyl)-2,2,2-trichloroacetimidate (146285-52-1) → (R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-12-(4-pyridin-4-yl-benzyloxy)-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid methyl ester (219596-45-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 70 percent / F₃CSO₃H; 4 Angstroem mol. sieves / CCl₄; cyclohexane / 3 h / 20 °C

2.1: Pd(PPh₃)4 / toluene / 48 h / Heating

2.2: 70 percent / KOMe / methanol; tetrahydrofuran / 1 h / 20 °C

With trifluorormethanesulfonic acid; 4 A molecular sieve; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrachloromethane; cyclohexane; toluene; 2.1: Stille reaction;

DOI:10.1016/S0040-4039(00)01866-9

upstream raw materials:

4-trimethylstannyl-pyridine

methyl 3α-acetoxy-12α-hydroxy-5β-cholan-24-oate

(4-bromobenzyl)-2,2,2-trichloroacetimidate

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