methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[(p-azidomethyl)phenyl]-7α,12α-bis(formyloxy)-5β-cholan-24-oate

Base Information

Chemical Name:methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[(p-azidomethyl)phenyl]-7α,12α-bis(formyloxy)-5β-cholan-24-oate
CAS No.:198016-04-5
Molecular Formula:C₄₅H₆₅N₃O₁₀
Molecular Weight:808.025
Hs Code.:

Synonyms:methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[(p-azidomethyl)phenyl]-7α,12α-bis(formyloxy)-5β-cholan-24-oate

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Chemical Property of methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[(p-azidomethyl)phenyl]-7α,12α-bis(formyloxy)-5β-cholan-24-oate

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Technology Process of methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[(p-azidomethyl)phenyl]-7α,12α-bis(formyloxy)-5β-cholan-24-oate

There total 9 articles about methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[(p-azidomethyl)phenyl]-7α,12α-bis(formyloxy)-5β-cholan-24-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:

: 124-63-0
methanesulfonyl chloride

: 198016-03-4
methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[(p-hydroxymethyl)phenyl]-7α,12α-bis(formyloxy)-5β-cholan-24-oate

: 198016-04-5
methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[(p-azidomethyl)phenyl]-7α,12α-bis(formyloxy)-5β-cholan-24-oate

Guidance literature:: methanesulfonyl chloride; methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[(p-hydroxymethyl)phenyl]-7α,12α-bis(formyloxy)-5β-cholan-24-oate; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -14 - 0 ℃; for 1h;

With N,N,N',N'-tetramethylguanidinium azide; In dichloromethane; at 0 - 30 ℃; for 0.5h;
DOI:10.1021/jo971272w

Reference yield:

: 81-25-4
cholic acid

: 198016-04-5
methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[(p-azidomethyl)phenyl]-7α,12α-bis(formyloxy)-5β-cholan-24-oate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 92 percent / HClO₄; Ac₂O

2.1: CH₂Cl₂; methanol / -5 - 0 °C

3.1: 18 g / sodium bicarbonate / methanol / 1.8 h / 0 °C

4.1: 87 percent / silica gel; pyridinium chlorochromate / CH₂Cl₂ / 2 h

5.1: 93 percent / SbBu₃ / tetrahydrofuran / 60 - 65 °C

6.1: magnesium / tetrahydrofuran / 1 h / sonication

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

6.3: 87 percent / tetrahydrofuran / -60 - 20 °C

7.1: CH₂Cl₂ / 5 h / 50 °C

8.1: 3.87 g / aq. ammonia / CH₂Cl₂; diethyl ether / 5 h

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

9.2: 3.8 g / N,N,N',N'-tetramethylguanidinium azide / CH₂Cl₂ / 0.5 h / 0 - 30 °C

With ammonium hydroxide; perchloric acid; acetic anhydride; silica gel; tributylstibine; sodium hydrogencarbonate; magnesium; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 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;
DOI:10.1021/jo971272w

Reference yield:

: 2097-89-4
cholic acid triformate

: 198016-04-5
methyl 3β-[bis(butoxycarbonyl)methyl]-3α-[(p-azidomethyl)phenyl]-7α,12α-bis(formyloxy)-5β-cholan-24-oate

Guidance literature:: Multi-step reaction with 8 steps

1.1: CH₂Cl₂; methanol / -5 - 0 °C

2.1: 18 g / sodium bicarbonate / methanol / 1.8 h / 0 °C

3.1: 87 percent / silica gel; pyridinium chlorochromate / CH₂Cl₂ / 2 h

4.1: 93 percent / SbBu₃ / tetrahydrofuran / 60 - 65 °C

5.1: magnesium / tetrahydrofuran / 1 h / sonication

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

5.3: 87 percent / tetrahydrofuran / -60 - 20 °C

6.1: CH₂Cl₂ / 5 h / 50 °C

7.1: 3.87 g / aq. ammonia / CH₂Cl₂; diethyl ether / 5 h

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

8.2: 3.8 g / N,N,N',N'-tetramethylguanidinium azide / CH₂Cl₂ / 0.5 h / 0 - 30 °C

With ammonium hydroxide; silica gel; tributylstibine; sodium hydrogencarbonate; magnesium; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 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;
DOI:10.1021/jo971272w