3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethynyl phosphonic acid diethyl ester

Base Information

• Chemical Name: 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethynyl phosphonic acid diethyl ester
• CAS No.: 948907-54-8
• Molecular Formula: C₃₄H₄₈NO₇P
• Molecular Weight: 613.731
• Mol file: 948907-54-8.mol

Synonyms:3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethynyl phosphonic acid diethyl ester

Chemical Property of 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethynyl phosphonic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethynyl phosphonic acid diethyl ester

There total 4 articles about 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethynyl phosphonic acid diethyl ester 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: 89.0%

diethyl chlorophosphate (814-49-3) + 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne (91934-95-1) → 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethynyl phosphonic acid diethyl ester (948907-54-8)

Guidance literature:

3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne; With lithium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 1h;

diethyl chlorophosphate; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1016/j.steroids.2006.07.003

Reference yield:

(5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one (39931-88-9,116003-08-8,39931-87-8) → 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethynyl phosphonic acid diethyl ester (948907-54-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 45 percent / CuCl / tetrahydrofuran / 1 h / 20 °C

2.1: 90 percent / tetrahydrofuran / 16 h / 20 °C

3.1: LiHMDS / tetrahydrofuran / 1 h / 20 °C

3.2: 89 percent / tetrahydrofuran / 16 h / 20 °C

With copper(l) chloride; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/j.steroids.2006.07.003

Reference yield:

ethylene deltenone (5571-36-8) → 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethynyl phosphonic acid diethyl ester (948907-54-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 36 percent / NaHCO₃; mCPBA / CH₂Cl₂ / 0.5 h / -40 °C

2.1: 45 percent / CuCl / tetrahydrofuran / 1 h / 20 °C

3.1: 90 percent / tetrahydrofuran / 16 h / 20 °C

4.1: LiHMDS / tetrahydrofuran / 1 h / 20 °C

4.2: 89 percent / tetrahydrofuran / 16 h / 20 °C

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; copper(l) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.steroids.2006.07.003

upstream raw materials:

diethyl chlorophosphate

3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-ethyne

(5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one

ethylene deltenone