methyl 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: methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate
• CAS No.: 198016-19-2
• Molecular Formula: C₄₉H₇₃NO₁₂
• Molecular Weight: 868.118
• Mol file: 198016-19-2.mol

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

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

There total 11 articles about methyl 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) → methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate (198016-19-2)

Guidance literature:

Multi-step reaction with 11 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

With ammonium hydroxide; perchloric acid; acetic anhydride; silica gel; tributylstibine; sodium hydrogencarbonate; magnesium; N-ethyl-N,N-diisopropylamine; 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;

DOI:10.1021/jo971272w

Reference yield:

24-norcholic acid triformate (68777-19-5) → methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate (198016-19-2)

Guidance literature:

Multi-step reaction with 10 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

With ammonium hydroxide; silica gel; tributylstibine; sodium hydrogencarbonate; magnesium; N-ethyl-N,N-diisopropylamine; 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;

DOI:10.1021/jo971272w

Reference yield:

methyl 3-oxo-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate (198016-13-6) → methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-23-oate (198016-19-2)

Guidance literature:

Multi-step reaction with 7 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

With ammonium hydroxide; tributylstibine; magnesium; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; 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;

DOI:10.1021/jo971272w

upstream raw materials:

di-tert-butyl dicarbonate

24-norcholic acid

24-norcholic acid triformate

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

Downstream raw materials:

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