3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene

Base Information

• Chemical Name: 3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene
• CAS No.: 3589-91-1
• Molecular Formula: C₂₈H₄₀O₄
• Molecular Weight: 440.623
• Mol file: 3589-91-1.mol

Synonyms:3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene

Chemical Property of 3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene

There total 1 articles about 3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene 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: 85.0%

3,4-dihydro-2H-pyran (110-87-2) + estradiol (50-28-2) → 3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene (3589-91-1) + Estradiol-3-tetrahydropyranylether (41781-86-6)

Guidance literature:

With basic resin Amberlite IRA-400 (iodide form); In dichloromethane; at 20 ℃; for 0.133333h;

Reference yield:

3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene (3589-91-1) → C48H62(2)H4NO6P

Guidance literature:

Multi-step reaction with 11 steps

1.1: LDA; t-BuOK / hexane; tetrahydrofuran / 3.5 h / -78 °C

1.2: (MeO)3B / hexane; tetrahydrofuran / 2 h

1.3: aq. H₂O₂ / hexane; tetrahydrofuran / 1 h / 20 °C

2.1: 1.82 g / pyridinium chlorochromate / CH₂Cl₂ / 2.33 h

3.1: 47 percent / KOtBu; Et₃B / diethyl ether; tetrahydrofuran / 20 °C

4.1: CH₃COCl / methanol / 0.5 h / 20 °C

5.1: 0.66 g / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 14 h / 20 °C

6.1: 77 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.5 h / Heating

7.1: BH₃ / tetrahydrofuran / 14 h / 20 °C

7.2: 66 percent / aq. H₂O₂; aq. KOH / tetrahydrofuran / 3 h

8.1: diisopropylethylamine / tetrahydrofuran / 1 h / 0 - 2 °C

9.1: 0.48 g / LiBr / dimethylformamide / 1 h / 50 - 60 °C

10.1: NaH; nBu₄NBr / benzene / 80 °C

11.1: TBAF / tetrahydrofuran / 20 °C

With triethylsilane; triethyl borane; boron trifluoride diethyl etherate; borane; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; pyridinium p-toluenesulfonate; sodium hydride; N-ethyl-N,N-diisopropylamine; acetyl chloride; pyridinium chlorochromate; lithium bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja017344p

Reference yield:

3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene (3589-91-1) → C55H65(2)H4N2O10P

Guidance literature:

Multi-step reaction with 12 steps

1.1: LDA; t-BuOK / hexane; tetrahydrofuran / 3.5 h / -78 °C

1.2: (MeO)3B / hexane; tetrahydrofuran / 2 h

1.3: aq. H₂O₂ / hexane; tetrahydrofuran / 1 h / 20 °C

2.1: 1.82 g / pyridinium chlorochromate / CH₂Cl₂ / 2.33 h

3.1: 47 percent / KOtBu; Et₃B / diethyl ether; tetrahydrofuran / 20 °C

4.1: CH₃COCl / methanol / 0.5 h / 20 °C

5.1: 0.66 g / Et₃SiH; BF₃*Et₂O / CH₂Cl₂ / 14 h / 20 °C

6.1: 77 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.5 h / Heating

7.1: BH₃ / tetrahydrofuran / 14 h / 20 °C

7.2: 66 percent / aq. H₂O₂; aq. KOH / tetrahydrofuran / 3 h

8.1: diisopropylethylamine / tetrahydrofuran / 1 h / 0 - 2 °C

9.1: 0.48 g / LiBr / dimethylformamide / 1 h / 50 - 60 °C

10.1: NaH; nBu₄NBr / benzene / 80 °C

11.1: TBAF / tetrahydrofuran / 20 °C

12.1: diisopropylethylamine / tetrahydrofuran / 2 h / 20 °C

With triethylsilane; triethyl borane; boron trifluoride diethyl etherate; borane; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; pyridinium p-toluenesulfonate; sodium hydride; N-ethyl-N,N-diisopropylamine; acetyl chloride; pyridinium chlorochromate; lithium bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1021/ja017344p

upstream raw materials:

3,4-dihydro-2H-pyran

estradiol

Downstream raw materials:

estradiol 17β-tetrahydropyranyl ether

(8R,9S,13S,14S,17S)-13-Methyl-3,17-bis-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-ol

N-butyl-N-methyl-7-(3-benzyloxy-17-oxoestra-1,3,5(10)-trien-6β-yl)heptanamide

N-butyl-N-methyl-7-(3-benzyloxy-17β-hydroxy-2-methoxyestra-1,3,5(10)-trien-6β-yl)heptanamide

Refernces