Estrone 17-Ethylene Ketal

Base Information

• Chemical Name: Estrone 17-Ethylene Ketal
• CAS No.: 900-83-4
• Molecular Formula: C₂₀H₂₆O₃
• Molecular Weight: 314.425
• Mol file: 900-83-4.mol

Synonyms:(8R,9S,13S,14S)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2′-[1,3]dioxolan]-3-ol

Chemical Property of Estrone 17-Ethylene Ketal

Chemical Property:

• Solubility.: Chloroform, Dichloromethane

Purity/Quality:

Estrone17-EthyleneKetal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Estrone 17-Ethylene Ketal is a Protected Estrone (E889050) used in the preparation of A-ring substituted estrogen derivatives as antitumor agents.

Technology Process of Estrone 17-Ethylene Ketal

There total 1 articles about Estrone 17-Ethylene Ketal 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: 82.0%

estradiol (50-28-2) + ethylene glycol (107-21-1) → Estrone (53-16-7) + (8R,9S,13S,14S)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2′-[1,3]dioxolan]-3-ol (900-83-4)

Guidance literature:

With dimethyl sulfoxide; [ReOCl₃(PPh₃)₂]; In toluene; for 5h; Heating;

DOI:10.1021/ol990755e

Reference yield: 100.0%

(8R,9S,13S,14S)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2′-[1,3]dioxolan]-3-ol (900-83-4) + methyl iodide (74-88-4) → 17,17-ethylenedioxy-3-methoxyoestra-1,3,5(10)-triene (28336-29-0)

Guidance literature:

(8R,9S,13S,14S)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2′-[1,3]dioxolan]-3-ol; With sodium hydride; In tetrahydrofuran; for 0.5h; Inert atmosphere; Reflux;

methyl iodide; In tetrahydrofuran; for 1h; Inert atmosphere;

DOI:10.1016/j.steroids.2018.11.018

Reference yield:

(8R,9S,13S,14S)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrospiro[cyclopenta[a]phenanthrene-17,2′-[1,3]dioxolan]-3-ol (900-83-4) → 2-methoxyestrone (362-08-3,7683-30-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaH / dimethylformamide / 0 °C

1.2: 19.5 g / dimethylformamide / 16 h / 20 °C

2.1: sec-BuLi / tetrahydrofuran / 2 h / -78 °C

2.2: 86 percent / tetrahydrofuran / 1 h / -78 - 0 °C

3.1: Na₂HPO₄; m-chloroperbenzoic acid / CH₂Cl₂; CHCl₃ / 1 h / 20 °C

4.1: 13.8 g / NaOH / methanol / 2 h

5.1: K₂CO₃; tetrabutylammonium iodide / dimethylformamide / 72 h / 20 °C

6.1: 1.45 g / aq. HCl / tetrahydrofuran / 1 h

With hydrogenchloride; sodium hydroxide; disodium hydrogenphosphate; sec.-butyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; 3.1: Baeyer-Villiger oxidation;

DOI:10.1021/jm050066a

upstream raw materials:

estradiol

ethylene glycol

Downstream raw materials:

opt.-inakt. 17-Ethylendioxy-3-methoxy-oestra-(1,3,5(10))-trien

2-methoxyestrone

6-dehydroestrone

6-Dehydroestradiol

Refernces