19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol

Base Information

• Chemical Name: 19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol
• CAS No.: 4717-38-8
• Molecular Formula: C20H24O2
• Molecular Weight: 296.409
• Mol file: 4717-38-8.mol

Synonyms:6|A-Hydroxy Ethynyl Estradiol;

Chemical Property of 19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol

Chemical Property:

• Boiling Point: 457.2°Cat760mmHg
• PKA: 10.24±0.60(Predicted)
• Flash Point: 211.2°C
• PSA: 40.46000
• Density: 1.21g/cm³
• LogP: 3.61260

Purity/Quality:

99%, ^*data from raw suppliers

17-epi-EthynylEstradiol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: The epimer derivative of Ethynyl Estradiol (E685100). An impurity.

Technology Process of 19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol

There total 12 articles about 19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol 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: 76.0%

(8R,9S,13S,14S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-17-ethynyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol (206442-61-7) → 17-beta-Ethynylestradiol (4717-38-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1.5h; Ambient temperature;

DOI:10.1016/S0040-4020(98)00124-0

Reference yield:

ammonium chloride + 3-methoxy-19-norpregna-1,3,5(10)-triene-20-yn-17α-ol (4502-08-3) → 17-beta-Ethynylestradiol (4717-38-8)

Guidance literature:

With methyl magnesium iodide; In ethyl acetate; benzene;

Reference yield:

3-tert-butyldimethylsilyloxy-17α,20R-epoxy-20-chloromethyl-1,3,5(10),17(20)estratetraene → 17-beta-Ethynylestradiol (4717-38-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -35 °C

2: 76 percent / Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

With n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4020(98)00124-0

upstream raw materials:

(8R,9S,13S,14S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-17-ethynyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol

2-[3-(tert-butyl-dimethyl-silanoxy)-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydrocyclopenta[a]phenanthren-17-ylidene]-ethanol

3-tert-butyldimethylsilyloxy-17α,20R-epoxy-20-hydroxymethyl-1,3,5(10),17(20)estratetraene

3-methoxy-19-norpregna-1,3,5(10)-triene-20-yn-17α-ol

Refernces

• 1、 -. "Pharmaceutical composition with tumor necrosis factor A and 2-methoxyestrone-3-0-sulphamate for inhibition of estrone sulphatase". . . Retrieved 2008/06/13.
• 2、 -. "Halogenated sulphamate-, phosphonate-, thiophosphonate-, sulphonate- and sulphonamide- compounds as inhibitors of steroid sulphatase". . . Retrieved 2008/06/13.