Benzoic acid (3S,5S,7S,8S,9S,10R,14S,16S)-17-furan-3-yl-3-hydroxy-7-methoxymethoxy-4,4,8,10-tetramethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

Base Information

• Chemical Name: Benzoic acid (3S,5S,7S,8S,9S,10R,14S,16S)-17-furan-3-yl-3-hydroxy-7-methoxymethoxy-4,4,8,10-tetramethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester
• CAS No.: 125417-30-3
• Molecular Formula: C₃₄H₄₄O₆
• Molecular Weight: 548.72
• Mol file: 125417-30-3.mol

Synonyms:

Chemical Property of Benzoic acid (3S,5S,7S,8S,9S,10R,14S,16S)-17-furan-3-yl-3-hydroxy-7-methoxymethoxy-4,4,8,10-tetramethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (3S,5S,7S,8S,9S,10R,14S,16S)-17-furan-3-yl-3-hydroxy-7-methoxymethoxy-4,4,8,10-tetramethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

There total 14 articles about Benzoic acid (3S,5S,7S,8S,9S,10R,14S,16S)-17-furan-3-yl-3-hydroxy-7-methoxymethoxy-4,4,8,10-tetramethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-16-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:

(3S,5S,7S,8S,9S,10R,14S,16R)-17-Furan-3-yl-7-methoxymethoxy-4,4,8,10-tetramethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol (125417-29-0,125417-31-4) + benzoic acid (65-85-0,8013-63-6) → Benzoic acid (3S,5S,7S,8S,9S,10R,14S,16S)-17-furan-3-yl-3-hydroxy-7-methoxymethoxy-4,4,8,10-tetramethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester (125417-30-3)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 23 ℃; for 3h;

DOI:10.1016/S0040-4039(00)99392-4

Reference yield:

1-(3-furyl)-2-nitroethane (122016-41-5) → Benzoic acid (3S,5S,7S,8S,9S,10R,14S,16S)-17-furan-3-yl-3-hydroxy-7-methoxymethoxy-4,4,8,10-tetramethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester (125417-30-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) sodium ethoxide; 2.) 12N HCl / 1.) EtOH, reflux, 20 min.; 2.) 10 deg C

2: 92 percent / 1 M sodium ethoxide / ethanol / 0.75 h / 70 °C

3: 92 percent / tetrabutylammonium iodide, diisopropylethylamine / acetonitrile / 7 h / 70 °C

4: lithium tri-sec-butylborohydride / tetrahydrofuran / 0.5 h / -78 °C

5: diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 3 h / 23 °C

With hydrogenchloride; sodium ethanolate; tetra-(n-butyl)ammonium iodide; L-Selectride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; acetonitrile;

DOI:10.1016/S0040-4039(00)99392-4

Reference yield:

(1R,4aS,4bS,8aS,10aS)-7-Hydroxy-4b,8,8,10a-tetramethyl-2-oxo-tetradecahydro-phenanthrene-1-carboxylic acid methyl ester → Benzoic acid (3S,5S,7S,8S,9S,10R,14S,16S)-17-furan-3-yl-3-hydroxy-7-methoxymethoxy-4,4,8,10-tetramethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester (125417-30-3)

Guidance literature:

Multi-step reaction with 13 steps

1: 86 percent / aq. CrO₃, sulfuric acid / acetone / 0 °C

2: 1.) sodium hydride / 1.) reflux, THF, 1 h; 2.) 0 deg C, 10 min

3: 87 percent / p-toluenesulfonic acid / benzene / Heating

4: 90 percent / diisobutylaluminium hydride / toluene / 0.5 h / -20 °C

5: HO₃SONO / pyridine / 0.5 h / 0 °C

6: 28 percent / CH₂Cl₂ / 50 °C / Irradiation

7: 1 N HCl, acetaldehyde / 12 h / 23 °C

8: tetramethylammonium triacetoxyborohydride / acetone; acetic acid / 0.33 h / -78 °C

9: 1.) sodium ethoxide; 2.) 12N HCl / 1.) EtOH, reflux, 20 min.; 2.) 10 deg C

10: 92 percent / 1 M sodium ethoxide / ethanol / 0.75 h / 70 °C

11: 92 percent / tetrabutylammonium iodide, diisopropylethylamine / acetonitrile / 7 h / 70 °C

12: lithium tri-sec-butylborohydride / tetrahydrofuran / 0.5 h / -78 °C

13: diethyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 3 h / 23 °C

With chromium(VI) oxide; hydrogenchloride; nitrosylsulfuric acid; sulfuric acid; sodium ethanolate; tetra-(n-butyl)ammonium iodide; L-Selectride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetaldehyde; N-ethyl-N,N-diisopropylamine; triphenylphosphine; tetramethylammonium triacetoxyborohydride; diethylazodicarboxylate; In tetrahydrofuran; pyridine; ethanol; dichloromethane; acetic acid; acetone; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)99392-4

upstream raw materials:

(3S,5S,7S,8S,9S,10R,14S,16R)-17-Furan-3-yl-7-methoxymethoxy-4,4,8,10-tetramethyl-2,3,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol

benzoic acid

1-(3-furyl)-2-nitroethane

(1R,4aS,4bS,8aS,10aS)-4b,8,8,10a-Tetramethyl-2,7-dioxo-tetradecahydro-phenanthrene-1-carboxylic acid methyl ester