(17β)-17-acetoxy-3-(2'-benzoyl-4'-nitrophenyloxy)-2-benzyloxy-1,3,5(10)-estratriene

Base Information

• Chemical Name: (17β)-17-acetoxy-3-(2'-benzoyl-4'-nitrophenyloxy)-2-benzyloxy-1,3,5(10)-estratriene
• CAS No.: 176219-90-2
• Molecular Formula: C₄₀H₃₉NO₇
• Molecular Weight: 645.752
• Mol file: 176219-90-2.mol

Synonyms:(17β)-17-acetoxy-3-(2'-benzoyl-4'-nitrophenyloxy)-2-benzyloxy-1,3,5(10)-estratriene

Chemical Property of (17β)-17-acetoxy-3-(2'-benzoyl-4'-nitrophenyloxy)-2-benzyloxy-1,3,5(10)-estratriene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (17β)-17-acetoxy-3-(2'-benzoyl-4'-nitrophenyloxy)-2-benzyloxy-1,3,5(10)-estratriene

There total 1 articles about (17β)-17-acetoxy-3-(2'-benzoyl-4'-nitrophenyloxy)-2-benzyloxy-1,3,5(10)-estratriene 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: 99.6%

2-(17β-acetoxy-2-hydroxy-estra-1,3,5(10)-trien-3-yloxy)-5-nitro-benzophenone (38781-50-9) + benzyl chloride (100-44-7) → (17β)-17-acetoxy-3-(2'-benzoyl-4'-nitrophenyloxy)-2-benzyloxy-1,3,5(10)-estratriene (176219-90-2)

Guidance literature:

With sodium carbonate; In N,N-dimethyl-formamide; at 100 - 120 ℃; for 5h;

DOI:10.1271/bbb.60.405

Reference yield:

(17β)-17-acetoxy-3-(2'-benzoyl-4'-nitrophenyloxy)-2-benzyloxy-1,3,5(10)-estratriene (176219-90-2) → Acetic acid (8R,9S,13R,14S,15S,16S,17S)-16,17-diacetoxy-2,3-bis-benzyloxy-14-hydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-15-yl ester (176219-98-0)

Guidance literature:

Multi-step reaction with 9 steps

1: KOH / ethanol / 2 h / Heating

2: 224 mg / Na₂CO₃ / 20 h / 100 - 120 °C

3: 56.5 percent / Jones reagent / acetone / 0.05 h

4: 93 percent / Et₃N / CH₂Cl₂ / 2 h / -78 °C

5: 71.9 percent / Pd(OAc)2, Cu(OAc)2, oxygen / acetonitrile / 17 h / 50 °C

6: 59 percent / p-TsOH*H₂O / benzene / 0.07 h / Heating

7: 1) PBA, 2) Na₂CO₃ / 1) C₆H₆, CH₂Cl₂, 3 days, 2) t-BuOH, H₂O, reflux, 1 h

8: 82.7 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 1 h

9: 1) OsO₄, N-methylmorpholine N-oxide, H₂O, 2) pyridine, DMAP / 1) acetone, 4 days, 2) 17 h

With pyridine; dmap; palladium diacetate; potassium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; jones reagent; cerium(III) chloride; copper diacetate; water; oxygen; sodium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; acetonitrile; benzene;

DOI:10.1271/bbb.60.405

Reference yield:

(17β)-17-acetoxy-3-(2'-benzoyl-4'-nitrophenyloxy)-2-benzyloxy-1,3,5(10)-estratriene (176219-90-2) → (8R,9S,13R,14S,17R)-2,3-Bis-benzyloxy-13-methyl-6,7,8,9,11,12,13,17-octahydro-cyclopenta[a]phenanthrene-14,17-diol (176219-95-7)

Guidance literature:

Multi-step reaction with 8 steps

1: KOH / ethanol / 2 h / Heating

2: 224 mg / Na₂CO₃ / 20 h / 100 - 120 °C

3: 56.5 percent / Jones reagent / acetone / 0.05 h

4: 93 percent / Et₃N / CH₂Cl₂ / 2 h / -78 °C

5: 71.9 percent / Pd(OAc)2, Cu(OAc)2, oxygen / acetonitrile / 17 h / 50 °C

6: 59 percent / p-TsOH*H₂O / benzene / 0.07 h / Heating

7: 1) PBA, 2) Na₂CO₃ / 1) C₆H₆, CH₂Cl₂, 3 days, 2) t-BuOH, H₂O, reflux, 1 h

8: 82.7 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 1 h

With palladium diacetate; potassium hydroxide; sodium tetrahydroborate; jones reagent; cerium(III) chloride; copper diacetate; oxygen; sodium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; acetonitrile; benzene;

DOI:10.1271/bbb.60.405

upstream raw materials:

2-(17β-acetoxy-2-hydroxy-estra-1,3,5(10)-trien-3-yloxy)-5-nitro-benzophenone

benzyl chloride

Downstream raw materials:

(17β)-2-benzyloxy-1,3,5(10)-estratriene-3,17-diol

(17β)-2,3-dibenzyloxy-1,3,5(10)-estratriene-17-ol

2,3-dibenzyloxy-1,3,5⁽¹⁰⁾-estratriene-17-one

(8R,9S,13S)-2,3-Bis-benzyloxy-13-methyl-6,7,8,9,11,12,13,16-octahydro-cyclopenta[a]phenanthren-17-one