3-Methoxy-19-nor-17α-pregna-1,3,5(10),20-tetraene-21,17-carbolactone

Base Information

• Chemical Name: 3-Methoxy-19-nor-17α-pregna-1,3,5(10),20-tetraene-21,17-carbolactone
• CAS No.: 114702-37-3
• Molecular Formula: C₂₂H₂₆O₃
• Molecular Weight: 338.447
• Mol file: 114702-37-3.mol

Synonyms:

Chemical Property of 3-Methoxy-19-nor-17α-pregna-1,3,5(10),20-tetraene-21,17-carbolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Methoxy-19-nor-17α-pregna-1,3,5(10),20-tetraene-21,17-carbolactone

There total 7 articles about 3-Methoxy-19-nor-17α-pregna-1,3,5(10),20-tetraene-21,17-carbolactone 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:

(8R,9S,13S,14S,17S)-17-Hydroxy-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-17-carbaldehyde (21887-08-1) → 3-Methoxy-19-nor-17α-pregna-1,3,5(10),20-tetraene-21,17-carbolactone (114702-37-3)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N, DMAP

2: 89 percent / lithium 2,2,6,6-tetramethylpiperidide / tetrahydrofuran / -100 °C

3: 1.) MsCl; 2.) SiO₂ / 1.) pyridine, 0 deg C

With dmap; 2,2,6,6-tetramethylpiperidinyl-lithium; silica gel; methanesulfonyl chloride; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)93385-4

Reference yield:

estrone 3-methyl ether (1624-62-0) → 3-Methoxy-19-nor-17α-pregna-1,3,5(10),20-tetraene-21,17-carbolactone (114702-37-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.8 g / potassium t-butoxide / 2-methyl-propan-2-ol; tetrahydrofuran / 3 h / 18 °C

2: 680 mg / potassium t-butoxide / H₂O; tetrahydrofuran / 2 h / 20 °C

3: 53 percent / 4-(dimethylamino)pyridine, NEt₃ / 48 h / 25 °C

4: 89 percent / lithium 2,2,6,6-tetramethylpiperidide / diethyl ether; tetrahydrofuran / 0.5 h / -100 °C

5: 1) methanesulphonyl chloride, pyridine, 2) silica gel / 1) 20 deg C

With pyridine; dmap; potassium tert-butylate; 2,2,6,6-tetramethylpiperidinyl-lithium; silica gel; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; diethyl ether; water; tert-butyl alcohol;

DOI:10.1016/S0040-4020(01)87846-7

Reference yield:

C26H30O4S (89211-10-9) → 3-Methoxy-19-nor-17α-pregna-1,3,5(10),20-tetraene-21,17-carbolactone (114702-37-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 680 mg / potassium t-butoxide / H₂O; tetrahydrofuran / 2 h / 20 °C

2: 53 percent / 4-(dimethylamino)pyridine, NEt₃ / 48 h / 25 °C

3: 89 percent / lithium 2,2,6,6-tetramethylpiperidide / diethyl ether; tetrahydrofuran / 0.5 h / -100 °C

4: 1) methanesulphonyl chloride, pyridine, 2) silica gel / 1) 20 deg C

With pyridine; dmap; potassium tert-butylate; 2,2,6,6-tetramethylpiperidinyl-lithium; silica gel; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; diethyl ether; water;

DOI:10.1016/S0040-4020(01)87846-7

upstream raw materials:

17-hydroxy-3-methoxy-19,21,24-trinor-17βH-chola-1,3,5(10)-trien-20-yn-23-oic acid

20(R)-Hydroxy-3-methoxy-19-nor-17α-pregna-1,3,5(10)-triene-21,17-carbolactone

(8R,9S,13S,14S,17S)-17-Hydroxy-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-17-carbaldehyde

17β-Acetoxy-3-methoxyestra-1,3,5(10)-triene-17α-carbaldehyde

Downstream raw materials:

3-Methoxy-19-nor-17α-pregna-1,3,5(10)-triene-21,17-carbolactone