estratriene-2,3,14,15,16,17-hexaol

Base Information

• Chemical Name: estratriene-2,3,14,15,16,17-hexaol
• CAS No.: 176219-89-9
• Molecular Formula: C₁₈H₂₄O₆
• Molecular Weight: 336.385
• Mol file: 176219-89-9.mol

Synonyms:(14b,15a,16a,17a)-1,3,5(10)-Estratriene-2,3,14,15,16,17-hexol

Chemical Property of estratriene-2,3,14,15,16,17-hexaol

Chemical Property:

• Vapor Pressure: 1.34E-12mmHg at 25°C
• Boiling Point: 542.5°Cat760mmHg
• Flash Point: 255.4°C
• PSA: 0.00000
• Density: 1.551g/cm³
• LogP: 0.00000

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of estratriene-2,3,14,15,16,17-hexaol

There total 48 articles about estratriene-2,3,14,15,16,17-hexaol 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: 100.0%

(8R,9S,13R,14S,15R,16R,17S)-2,3-Bis-benzyloxy-13-methyl-6,7,8,9,11,12,13,15,16,17-decahydro-cyclopenta[a]phenanthrene-14,15,16,17-tetraol (176219-99-1) → (14β,15β,16β,17α)-1,3,5(10)-estratriene-2,3,14,15,16,17-hexaol (176219-89-9)

Guidance literature:

With hydrogen; palladium on barium sulfate; In ethyl acetate; for 72h;

DOI:10.1271/bbb.60.405

Reference yield: 100.0%

(8R,9S,13R,14S,15S,16S,17S)-2,3-Bis-benzyloxy-13-methyl-6,7,8,9,11,12,13,15,16,17-decahydro-cyclopenta[a]phenanthrene-14,15,16,17-tetraol (176220-00-1) → (14β,15α,16α,17α)-1,3,5(10)-estratriene-2,3,14,15,16,17-hexaol (176219-89-9)

Guidance literature:

With hydrogen; palladium on barium sulfate; In ethyl acetate; for 72h;

DOI:10.1271/bbb.60.405

Reference yield:

2-(17β-acetoxy-2-hydroxy-estra-1,3,5(10)-trien-3-yloxy)-5-nitro-benzophenone (38781-50-9) → (14β,15β,16β,17α)-1,3,5(10)-estratriene-2,3,14,15,16,17-hexaol (176219-89-9)

Guidance literature:

Multi-step reaction with 12 steps

1: 99.6 percent / Na₂CO₃ / dimethylformamide / 5 h / 100 - 120 °C

2: KOH / ethanol / 2 h / Heating

3: 224 mg / Na₂CO₃ / 20 h / 100 - 120 °C

4: 56.5 percent / Jones reagent / acetone / 0.05 h

5: 93 percent / Et₃N / CH₂Cl₂ / 2 h / -78 °C

6: 71.9 percent / Pd(OAc)2, Cu(OAc)2, oxygen / acetonitrile / 17 h / 50 °C

7: 59 percent / p-TsOH*H₂O / benzene / 0.07 h / Heating

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

9: 82.7 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 1 h

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

11: 98.9 percent / Na₂CO₃ / methanol; tetrahydrofuran; H₂O / 18 h

12: 100 percent / H₂ / Pd-BaSO₄ / ethyl acetate / 72 h

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

DOI:10.1271/bbb.60.405

upstream raw materials:

(8R,9S,13R,14S,15R,16R,17S)-2,3-Bis-benzyloxy-13-methyl-6,7,8,9,11,12,13,15,16,17-decahydro-cyclopenta[a]phenanthrene-14,15,16,17-tetraol

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

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

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

Refernces

• 1、 Sakakibara, Masayuki,Uchida, Aki Ogawa. "Syntheses of (14β,15β,16β,17α)- and (14β,15α,16α,17α)-1,3,5(10)-Estratriene-2,3,14,15, 16,17-hexaols, Possible Candidates for the Inagami-Tamura Endogenous Digitalis-like Factor, and Their Activity". . p. 405 - 410. Retrieved 2007/10/03.