1α,3β-dihydroxy-20(S)-(5-hydroxy-5-methylhexyloxy)-9,10-secopregna-5,7,10(19)-triene

Base Information

• Chemical Name: 1α,3β-dihydroxy-20(S)-(5-hydroxy-5-methylhexyloxy)-9,10-secopregna-5,7,10(19)-triene
• CAS No.: 131711-70-1
• Molecular Formula: C₂₈H₄₆O₄
• Molecular Weight: 446.671
• Mol file: 131711-70-1.mol

Synonyms:

Chemical Property of 1α,3β-dihydroxy-20(S)-(5-hydroxy-5-methylhexyloxy)-9,10-secopregna-5,7,10(19)-triene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1α,3β-dihydroxy-20(S)-(5-hydroxy-5-methylhexyloxy)-9,10-secopregna-5,7,10(19)-triene

There total 7 articles about 1α,3β-dihydroxy-20(S)-(5-hydroxy-5-methylhexyloxy)-9,10-secopregna-5,7,10(19)-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:

2-(4-Bromobutyl)-2-methyl-1,3-dioxolane (20210-14-4) → 1α,3β-dihydroxy-20(S)-(5-hydroxy-5-methylhexyloxy)-9,10-secopregna-5,7,10(19)-triene (131711-70-1,132014-43-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / NaH / xylene / 18 h / Heating

2: Amberlyst 15 / methanol / 18 h / Ambient temperature

3: tetrahydrofuran; diethyl ether / 1.) 0 deg C, 30 min, 2.) RT, 40 min

4: 71 percent / n-Bu₄NF / tetrahydrofuran / 18 h / Heating

5: 1.) ethanol, irrad., 3 min, 2.) ethanol, reflux, 1.5 h

With Amberlyst 15; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; methanol; diethyl ether; xylene;

DOI:10.1248/cpb.40.1494

Reference yield:

1-[1,3-bis-(tert-butyldimethylsilanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanol (103909-74-6) → 1α,3β-dihydroxy-20(S)-(5-hydroxy-5-methylhexyloxy)-9,10-secopregna-5,7,10(19)-triene (131711-70-1,132014-43-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / NaH / xylene / 18 h / Heating

2: Amberlyst 15 / methanol / 18 h / Ambient temperature

3: tetrahydrofuran; diethyl ether / 1.) 0 deg C, 30 min, 2.) RT, 40 min

4: 71 percent / n-Bu₄NF / tetrahydrofuran / 18 h / Heating

5: 1.) ethanol, irrad., 3 min, 2.) ethanol, reflux, 1.5 h

With Amberlyst 15; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; methanol; diethyl ether; xylene;

DOI:10.1248/cpb.40.1494

Reference yield:

6-{(S)-1-[(1S,3R,9S,10R,13S,14R,17S)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethoxy}-hexan-2-one (137589-71-0) → 1α,3β-dihydroxy-20(S)-(5-hydroxy-5-methylhexyloxy)-9,10-secopregna-5,7,10(19)-triene (131711-70-1,132014-43-8)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran; diethyl ether / 1.) 0 deg C, 30 min, 2.) RT, 40 min

2: 71 percent / n-Bu₄NF / tetrahydrofuran / 18 h / Heating

3: 1.) ethanol, irrad., 3 min, 2.) ethanol, reflux, 1.5 h

With tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether;

DOI:10.1248/cpb.40.1494

upstream raw materials:

1α,3β-dihydroxy-20(S)-(5-hydroxy-5-methylhexyloxy)pregna-5,7-diene

2-(4-Bromobutyl)-2-methyl-1,3-dioxolane

1-[1,3-bis-(tert-butyldimethylsilanyloxy)-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanol

6-{(S)-1-[(1S,3R,9S,10R,13S,14R,17S)-1-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-10,13-dimethyl-2,3,4,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-ethoxy}-hexan-2-one

Refernces