3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-22(23)-ene

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Chemical Name:3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-22(23)-ene
CAS No.:198016-10-3
Molecular Formula:C₄₈H₇₁NO₁₀
Molecular Weight:822.092
Hs Code.:

Synonyms:3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-22(23)-ene

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Chemical Property of 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-22(23)-ene

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Technology Process of 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-22(23)-ene

There total 12 articles about 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-22(23)-ene 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:

: 24424-99-5
di-tert-butyl dicarbonate

: 2-[(3R,5S,7R,8R,9S,10S,12S,13R,14S,17R)-3-(4-Aminomethyl-phenyl)-7,12-diformyloxy-10,13-dimethyl-17-((R)-1-methyl-allyl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl]-malonic acid dibutyl ester

: 198016-10-3
3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-22(23)-ene

Guidance literature:: With triethylamine; In tetrahydrofuran; water; at 20 ℃;
DOI:10.1021/jo971272w

Reference yield:

: 81-25-4
cholic acid

: 198016-10-3
3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-22(23)-ene

Guidance literature:: Multi-step reaction with 12 steps

1.1: 92 percent / HClO₄; Ac₂O

2.1: 76 percent / cupric acetate monohydrate; pyridine; lead tetraacetate / benzene / 4 h / 40 - 90 °C

3.1: 97.8 percent / sodium acetate trihydrate / methanol / 96 h

4.1: 0.035 g / silica gel; pyridinium chlorochromate / CH₂Cl₂ / 2 h

5.1: 70 percent / SbBu₃ / tetrahydrofuran / 60 - 65 °C

6.1: magnesium / tetrahydrofuran / 1 h / sonication

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

6.3: 70 percent / tetrahydrofuran / -60 - 20 °C

7.1: CH₂Cl₂ / 5 h / 50 °C

8.1: 7.11 g / aq. ammonia / CH₂Cl₂; diethyl ether / 5 h

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

10.1: 0.535 g / N,N,N',N'-tetramethylguanidinium azide / CH₂Cl₂ / 0.5 h / 0 - 30 °C

11.1: triphenylphosphine / tetrahydrofuran; H₂O / 60 °C

12.1: 6.10 g / triethylamine / tetrahydrofuran; H₂O / 20 °C

With pyridine; lead(IV) acetate; ammonium hydroxide; perchloric acid; N,N,N',N'-tetramethylguanidinium azide; copper diacetate; sodium acetate; acetic anhydride; silica gel; tributylstibine; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; benzene; 1.1: Esterification / 2.1: Decarboxylation / 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: mesylation / 10.1: Substitution / 11.1: Reduction / 12.1: Acylation;
DOI:10.1021/jo971272w

Reference yield:

: 2097-89-4
cholic acid triformate

: 198016-10-3
3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-24-nor-5β-cholan-22(23)-ene

Guidance literature:: Multi-step reaction with 11 steps

1.1: 76 percent / cupric acetate monohydrate; pyridine; lead tetraacetate / benzene / 4 h / 40 - 90 °C

2.1: 97.8 percent / sodium acetate trihydrate / methanol / 96 h

3.1: 0.035 g / silica gel; pyridinium chlorochromate / CH₂Cl₂ / 2 h

4.1: 70 percent / SbBu₃ / tetrahydrofuran / 60 - 65 °C

5.1: magnesium / tetrahydrofuran / 1 h / sonication

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

5.3: 70 percent / tetrahydrofuran / -60 - 20 °C

6.1: CH₂Cl₂ / 5 h / 50 °C

7.1: 7.11 g / aq. ammonia / CH₂Cl₂; diethyl ether / 5 h

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

9.1: 0.535 g / N,N,N',N'-tetramethylguanidinium azide / CH₂Cl₂ / 0.5 h / 0 - 30 °C

10.1: triphenylphosphine / tetrahydrofuran; H₂O / 60 °C

11.1: 6.10 g / triethylamine / tetrahydrofuran; H₂O / 20 °C

With pyridine; lead(IV) acetate; ammonium hydroxide; N,N,N',N'-tetramethylguanidinium azide; copper diacetate; sodium acetate; silica gel; tributylstibine; magnesium; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; benzene; 1.1: Decarboxylation / 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: mesylation / 9.1: Substitution / 10.1: Reduction / 11.1: Acylation;
DOI:10.1021/jo971272w