(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2,4-Dinitro-benzenesulfonylamino)-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester

Base Information

• Chemical Name: (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2,4-Dinitro-benzenesulfonylamino)-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester
• CAS No.: 452303-22-9
• Molecular Formula: C₅₀H₈₃N₃O₁₀S
• Molecular Weight: 918.289

Synonyms:(R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2,4-Dinitro-benzenesulfonylamino)-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester

Chemical Property of (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2,4-Dinitro-benzenesulfonylamino)-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester

Chemical Property:

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Technology Process of (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2,4-Dinitro-benzenesulfonylamino)-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester

There total 6 articles about (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2,4-Dinitro-benzenesulfonylamino)-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl 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:

2,4-dinitrobenzenesulfonyl chloride (1656-44-6) + (R)-4-((3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-Amino-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl)-pentanoic acid icosyl ester → (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2,4-Dinitro-benzenesulfonylamino)-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester (452303-22-9)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1002/1521-3765(20020503)8:9<2197::AID-CHEM2197>3.0.CO;2-J

Reference yield:

1-Bromoeicosane (4276-49-7) → (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2,4-Dinitro-benzenesulfonylamino)-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester (452303-22-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: aq. Cs₂CO₃ / methanol

1.2: 89 percent / NaI / dimethylformamide / 168000 h / 47 °C

2.1: 65 percent / Ph₃P; DEAD; Et₃N / tetrahydrofuran / 40 °C

3.1: 90 percent / NaN₃; N,N'-dimethyl-N,N'-propylene urea / 16 h / 40 °C

4.1: Zn; glac. AcOH / 8 h

5.1: 0.39 g / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium azide; caesium carbonate; acetic acid; triethylamine; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/1521-3765(20020503)8:9<2197::AID-CHEM2197>3.0.CO;2-J

Reference yield:

cholic acid (81-25-4) → (R)-4-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(2,4-Dinitro-benzenesulfonylamino)-7,12-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-pentanoic acid icosyl ester (452303-22-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: aq. Cs₂CO₃ / methanol

1.2: 89 percent / NaI / dimethylformamide / 168000 h / 47 °C

2.1: 65 percent / Ph₃P; DEAD; Et₃N / tetrahydrofuran / 40 °C

3.1: 90 percent / NaN₃; N,N'-dimethyl-N,N'-propylene urea / 16 h / 40 °C

4.1: Zn; glac. AcOH / 8 h

5.1: 0.39 g / Et₃N / CH₂Cl₂ / 2 h / 0 °C

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium azide; caesium carbonate; acetic acid; triethylamine; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/1521-3765(20020503)8:9<2197::AID-CHEM2197>3.0.CO;2-J

upstream raw materials:

2,4-dinitrobenzenesulfonyl chloride

1-Bromoeicosane

cholic acid

eicosanoyl 3α,7α,12α-trishydroxy-5β-cholan-24-oate

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