pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate

Base Information

• Chemical Name: pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate
• CAS No.: 198016-20-5
• Molecular Formula: C₅₄H₇₀F₅NO₁₂
• Molecular Weight: 1020.14
• Mol file: 198016-20-5.mol

Synonyms:

Chemical Property of pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate

There total 13 articles about pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate 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:

24-norcholic acid (60696-62-0) → pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate (198016-20-5)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 90 percent / HClO₄; Ac₂O

2.1: CH₂Cl₂; methanol / -5 - 0 °C

3.1: 13.84 g / sodium bicarbonate / methanol / 1.8 h / 0 °C

4.1: 86 percent / silica gel; pyridinium chlorochromate / CH₂Cl₂ / 2 h

5.1: 96 percent / SbBu₃ / tetrahydrofuran / 74 h / 60 - 65 °C

6.1: magnesium / tetrahydrofuran / 1 h / sonication

6.2: CuCN / tetrahydrofuran / -10 - 0 °C

6.3: 91 percent / tetrahydrofuran / -60 - 20 °C

7.1: CH₂Cl₂ / 5 h / 50 °C

8.1: 4.8 g / aq. ammonia / CH₂Cl₂; diethyl ether / 5 h

9.1: N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / -14 - 0 °C

9.2: 3.96 g / N,N,N',N'-tetramethylguanidinium azide / CH₂Cl₂ / 0.5 h / 0 - 30 °C

10.1: triphenylphosphine / tetrahydrofuran; H₂O / 1 h / 60 °C

11.1: 3.41 g / tetrahydrofuran; H₂O / 20 - 60 °C / sonication

12.1: aqueous sodium hydroxide / tetrahydrofuran; methanol / 24 h / 20 °C

13.1: conc. perchloric acid; acetic anhydride / 25 h / 40 - 50 °C

14.1: aqueous sodium bicarbonate / tetrahydrofuran; diethyl ether

15.1: 0.262 g / dicyclohexyl carbodiimide / CH₂Cl₂ / -10 °C

With ammonium hydroxide; sodium hydroxide; perchloric acid; acetic anhydride; silica gel; tributylstibine; sodium hydrogencarbonate; magnesium; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1.1: Esterification / 2.1: Methylation / 3.1: deformylation / 4.1: Oxidation / 5.1: Condensation / 6.1: Metallation / 6.2: transmetallation / 6.3: Addition / 7.1: Esterification / 8.1: Hydrolysis / 9.1: Chlorination / 9.2: Substitution / 10.1: Reduction / 11.1: Acylation / 12.1: Hydrolysis / 13.1: Formylation / 14.1: Acylation / 15.1: Esterification;

DOI:10.1021/jo971272w

Reference yield:

24-norcholic acid triformate (68777-19-5) → pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate (198016-20-5)

Guidance literature:

Multi-step reaction with 14 steps

1.1: CH₂Cl₂; methanol / -5 - 0 °C

2.1: 13.84 g / sodium bicarbonate / methanol / 1.8 h / 0 °C

3.1: 86 percent / silica gel; pyridinium chlorochromate / CH₂Cl₂ / 2 h

4.1: 96 percent / SbBu₃ / tetrahydrofuran / 74 h / 60 - 65 °C

5.1: magnesium / tetrahydrofuran / 1 h / sonication

5.2: CuCN / tetrahydrofuran / -10 - 0 °C

5.3: 91 percent / tetrahydrofuran / -60 - 20 °C

6.1: CH₂Cl₂ / 5 h / 50 °C

7.1: 4.8 g / aq. ammonia / CH₂Cl₂; diethyl ether / 5 h

8.1: N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / -14 - 0 °C

8.2: 3.96 g / N,N,N',N'-tetramethylguanidinium azide / CH₂Cl₂ / 0.5 h / 0 - 30 °C

9.1: triphenylphosphine / tetrahydrofuran; H₂O / 1 h / 60 °C

10.1: 3.41 g / tetrahydrofuran; H₂O / 20 - 60 °C / sonication

11.1: aqueous sodium hydroxide / tetrahydrofuran; methanol / 24 h / 20 °C

12.1: conc. perchloric acid; acetic anhydride / 25 h / 40 - 50 °C

13.1: aqueous sodium bicarbonate / tetrahydrofuran; diethyl ether

14.1: 0.262 g / dicyclohexyl carbodiimide / CH₂Cl₂ / -10 °C

With ammonium hydroxide; sodium hydroxide; perchloric acid; acetic anhydride; silica gel; tributylstibine; sodium hydrogencarbonate; magnesium; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1.1: Methylation / 2.1: deformylation / 3.1: Oxidation / 4.1: Condensation / 5.1: Metallation / 5.2: transmetallation / 5.3: Addition / 6.1: Esterification / 7.1: Hydrolysis / 8.1: Chlorination / 8.2: Substitution / 9.1: Reduction / 10.1: Acylation / 11.1: Hydrolysis / 12.1: Formylation / 13.1: Acylation / 14.1: Esterification;

DOI:10.1021/jo971272w

Reference yield:

methyl 3-oxo-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate (198016-13-6) → pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate (198016-20-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 96 percent / SbBu₃ / tetrahydrofuran / 74 h / 60 - 65 °C

2.1: magnesium / tetrahydrofuran / 1 h / sonication

2.2: CuCN / tetrahydrofuran / -10 - 0 °C

2.3: 91 percent / tetrahydrofuran / -60 - 20 °C

3.1: CH₂Cl₂ / 5 h / 50 °C

4.1: 4.8 g / aq. ammonia / CH₂Cl₂; diethyl ether / 5 h

5.1: N,N-diisopropylethylamine / CH₂Cl₂ / 1 h / -14 - 0 °C

5.2: 3.96 g / N,N,N',N'-tetramethylguanidinium azide / CH₂Cl₂ / 0.5 h / 0 - 30 °C

6.1: triphenylphosphine / tetrahydrofuran; H₂O / 1 h / 60 °C

7.1: 3.41 g / tetrahydrofuran; H₂O / 20 - 60 °C / sonication

8.1: aqueous sodium hydroxide / tetrahydrofuran; methanol / 24 h / 20 °C

9.1: conc. perchloric acid; acetic anhydride / 25 h / 40 - 50 °C

10.1: aqueous sodium bicarbonate / tetrahydrofuran; diethyl ether

11.1: 0.262 g / dicyclohexyl carbodiimide / CH₂Cl₂ / -10 °C

With ammonium hydroxide; sodium hydroxide; perchloric acid; acetic anhydride; tributylstibine; sodium hydrogencarbonate; magnesium; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1.1: Condensation / 2.1: Metallation / 2.2: transmetallation / 2.3: Addition / 3.1: Esterification / 4.1: Hydrolysis / 5.1: Chlorination / 5.2: Substitution / 6.1: Reduction / 7.1: Acylation / 8.1: Hydrolysis / 9.1: Formylation / 10.1: Acylation / 11.1: Esterification;

DOI:10.1021/jo971272w

upstream raw materials:

24-norcholic acid

24-norcholic acid triformate

methyl 3-oxo-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate

methyl 3α-hydroxy-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate