16alpha,17alpha-[(R)-Butylidenedioxy]-6alpha,9-difluoro-11beta-hydroxy-21-[2-oxotetrahydrofuran-3(S)-ylsulfanyl]pregn-4-ene-3,20-dione

Base Information

• Chemical Name: 16alpha,17alpha-[(R)-Butylidenedioxy]-6alpha,9-difluoro-11beta-hydroxy-21-[2-oxotetrahydrofuran-3(S)-ylsulfanyl]pregn-4-ene-3,20-dione
• CAS No.: 193408-42-3
• Molecular Formula: C₂₉H₃₈F₂O₇S
• Molecular Weight: 568.679
• Mol file: 193408-42-3.mol

Synonyms:

Chemical Property of 16alpha,17alpha-[(R)-Butylidenedioxy]-6alpha,9-difluoro-11beta-hydroxy-21-[2-oxotetrahydrofuran-3(S)-ylsulfanyl]pregn-4-ene-3,20-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 16alpha,17alpha-[(R)-Butylidenedioxy]-6alpha,9-difluoro-11beta-hydroxy-21-[2-oxotetrahydrofuran-3(S)-ylsulfanyl]pregn-4-ene-3,20-dione

There total 7 articles about 16alpha,17alpha-[(R)-Butylidenedioxy]-6alpha,9-difluoro-11beta-hydroxy-21-[2-oxotetrahydrofuran-3(S)-ylsulfanyl]pregn-4-ene-3,20-dione 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: 45.0%

2-mercapto-γ-butyrolactone (14032-62-3) + 16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-methylsulfonyloxypregn-4-ene-3,20-dione (193408-61-6) → 16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-[(3S)-2-oxotetrahydrofuran-3-ylsulfanyl]pregn-4-ene-3,20-dione (193408-42-3) + 16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-[(3R)-2-oxotetrahydrofuran-3-ylsulfanyl]pregn-4-ene-3,20-dione (193408-42-3)

Guidance literature:

2-mercapto-γ-butyrolactone; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.75h;

16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-methylsulfonyloxypregn-4-ene-3,20-dione; In tetrahydrofuran; at 0 - 21 ℃; for 1.5h; Further stages.;

DOI:10.1039/b200190j

Reference yield: 45.0%

2-mercapto-γ-butyrolactone (14032-62-3) + 16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-methylsulfonyloxypregn-4-ene-3,20-dione (193408-61-6) → 16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-[(3S)-2-oxotetrahydrofuran-3-ylsulfanyl]pregn-4-ene-3,20-dione (193408-42-3) + 16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-[(3R)-2-oxotetrahydrofuran-3-ylsulfanyl]pregn-4-ene-3,20-dione (193408-42-3)

Guidance literature:

2-mercapto-γ-butyrolactone; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.75h;

16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-methylsulfonyloxypregn-4-ene-3,20-dione; In tetrahydrofuran; at 0 - 21 ℃; for 1.5h; Further stages.;

DOI:10.1039/b200190j

Reference yield: 37.0%

methanesulfonic acid (3R)-2-oxotetrahydrofuran-3-yl ester (192057-37-7) + 16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-mercaptopregn-4-ene-3,20-dione (193408-66-1) → 16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-[(3S)-2-oxotetrahydrofuran-3-ylsulfanyl]pregn-4-ene-3,20-dione (193408-42-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1039/b200190j

upstream raw materials:

2-mercapto-γ-butyrolactone

16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-methylsulfonyloxypregn-4-ene-3,20-dione

methanesulfonic acid (3R)-2-oxotetrahydrofuran-3-yl ester

16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-mercaptopregn-4-ene-3,20-dione

Refernces

• 1、 -. "21-(2-oxo-tetrahydrofuran)-thio pregnane derivatives, a process for their production and pharmaceutical compositions containing them". . . Retrieved 2008/06/13.