pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-23,24-bisnor-5β-cholane-22-thiolate

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Chemical Name:pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-23,24-bisnor-5β-cholane-22-thiolate
CAS No.:198016-12-5
Molecular Formula:C₅₃H₆₈F₅NO₁₁S
Molecular Weight:1022.18
Hs Code.:

pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-23,24-bisnor-5β-cholane-22-thiolate

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Chemical Property of pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-23,24-bisnor-5β-cholane-22-thiolate

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Technology Process of pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-23,24-bisnor-5β-cholane-22-thiolate

There total 15 articles about pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-23,24-bisnor-5β-cholane-22-thiolate 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:

: 81-25-4
cholic acid

: 198016-12-5
pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-23,24-bisnor-5β-cholane-22-thiolate

Guidance literature:: Multi-step reaction with 16 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

13.1: 90 percent / pyridine; N-methylmorpholine N-oxide; Bu₄NOAc / OsO₄ / acetone; H₂O; dioxane / 20 - 40 °C

14.1: sodium metaperiodate / acetonitrile; H₂O

15.1: sulfamic acid; sodium chlorite / acetonitrile; H₂O / -20 - 0 °C

16.1: 1.123 g / dicyclohexyl carbodiimide / CH₂Cl₂ / -10 °C

With pyridine; lead(IV) acetate; ammonium hydroxide; sodium chlorite; sodium periodate; perchloric acid; N,N,N',N'-tetramethylguanidinium azide; aminosulfonic acid; copper diacetate; sodium acetate; tetrabutylammonium acetate; acetic anhydride; silica gel; tributylstibine; magnesium; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; pyridinium chlorochromate; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; acetone; acetonitrile; 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 / 13.1: Oxidation / 14.1: Oxidation / 15.1: Oxidation / 16.1: Esterification;
DOI:10.1021/jo971272w

Reference yield:

: 2097-89-4
cholic acid triformate

: 198016-12-5
pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-23,24-bisnor-5β-cholane-22-thiolate

Guidance literature:: Multi-step reaction with 15 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

12.1: 90 percent / pyridine; N-methylmorpholine N-oxide; Bu₄NOAc / OsO₄ / acetone; H₂O; dioxane / 20 - 40 °C

13.1: sodium metaperiodate / acetonitrile; H₂O

14.1: sulfamic acid; sodium chlorite / acetonitrile; H₂O / -20 - 0 °C

15.1: 1.123 g / dicyclohexyl carbodiimide / CH₂Cl₂ / -10 °C

With pyridine; lead(IV) acetate; ammonium hydroxide; sodium chlorite; sodium periodate; N,N,N',N'-tetramethylguanidinium azide; aminosulfonic acid; copper diacetate; sodium acetate; tetrabutylammonium acetate; silica gel; tributylstibine; magnesium; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; pyridinium chlorochromate; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; acetone; acetonitrile; 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 / 12.1: Oxidation / 13.1: Oxidation / 14.1: Oxidation / 15.1: Esterification;
DOI:10.1021/jo971272w

Reference yield:

: 67371-30-6
3α,7α,12α-tris(formyloxy)-24-nor-5β-chol-22(23)-ene

: 198016-12-5
pentafluorophenyl 3β-[bis(butoxycarbonyl)methyl]-3α-[[[p-(tert-butoxycarbonyl)amino]methyl]phenyl]-7α,12α-bis(formyloxy)-23,24-bisnor-5β-cholane-22-thiolate

Guidance literature:: Multi-step reaction with 14 steps

1.1: 97.8 percent / sodium acetate trihydrate / methanol / 96 h

2.1: 0.035 g / silica gel; pyridinium chlorochromate / CH₂Cl₂ / 2 h

3.1: 70 percent / SbBu₃ / tetrahydrofuran / 60 - 65 °C

4.1: magnesium / tetrahydrofuran / 1 h / sonication

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

4.3: 70 percent / tetrahydrofuran / -60 - 20 °C

5.1: CH₂Cl₂ / 5 h / 50 °C

6.1: 7.11 g / aq. ammonia / CH₂Cl₂; diethyl ether / 5 h

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

8.1: 0.535 g / N,N,N',N'-tetramethylguanidinium azide / CH₂Cl₂ / 0.5 h / 0 - 30 °C

9.1: triphenylphosphine / tetrahydrofuran; H₂O / 60 °C

10.1: 6.10 g / triethylamine / tetrahydrofuran; H₂O / 20 °C

11.1: 90 percent / pyridine; N-methylmorpholine N-oxide; Bu₄NOAc / OsO₄ / acetone; H₂O; dioxane / 20 - 40 °C

12.1: sodium metaperiodate / acetonitrile; H₂O

13.1: sulfamic acid; sodium chlorite / acetonitrile; H₂O / -20 - 0 °C

14.1: 1.123 g / dicyclohexyl carbodiimide / CH₂Cl₂ / -10 °C

With pyridine; ammonium hydroxide; sodium chlorite; sodium periodate; N,N,N',N'-tetramethylguanidinium azide; aminosulfonic acid; sodium acetate; tetrabutylammonium acetate; silica gel; tributylstibine; magnesium; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; triphenylphosphine; pyridinium chlorochromate; osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; acetone; acetonitrile; 1.1: deformylation / 2.1: Oxidation / 3.1: Condensation / 4.1: Metallation / 4.2: transmetallation / 4.3: Addition / 5.1: Esterification / 6.1: Hydrolysis / 7.1: mesylation / 8.1: Substitution / 9.1: Reduction / 10.1: Acylation / 11.1: Oxidation / 12.1: Oxidation / 13.1: Oxidation / 14.1: Esterification;
DOI:10.1021/jo971272w