(10S,11R,12S,15S,18S)-15-(Carbamoylmethyl)-10,11,23-trihydroxy-18-[3(R)-methyl-2-oxopentanamido]-9,14,17-trioxo-N-[1(Z)-propenyl]-8,13,16-triazatetracyclo[18.3.1.0(2,7).0(6,10)]tetracosa-1(24),2,4,6,20,22-hexaene-12-carboxamide

Base Information

• Chemical Name: (10S,11R,12S,15S,18S)-15-(Carbamoylmethyl)-10,11,23-trihydroxy-18-[3(R)-methyl-2-oxopentanamido]-9,14,17-trioxo-N-[1(Z)-propenyl]-8,13,16-triazatetracyclo[18.3.1.0(2,7).0(6,10)]tetracosa-1(24),2,4,6,20,22-hexaene-12-carboxamide
• CAS No.: 262854-05-7
• Molecular Formula: C₃₃H₃₈N₆O₁₀
• Molecular Weight: 678.699
• Mol file: 262854-05-7.mol

Synonyms:

Chemical Property of (10S,11R,12S,15S,18S)-15-(Carbamoylmethyl)-10,11,23-trihydroxy-18-[3(R)-methyl-2-oxopentanamido]-9,14,17-trioxo-N-[1(Z)-propenyl]-8,13,16-triazatetracyclo[18.3.1.0(2,7).0(6,10)]tetracosa-1(24),2,4,6,20,22-hexaene-12-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (10S,11R,12S,15S,18S)-15-(Carbamoylmethyl)-10,11,23-trihydroxy-18-[3(R)-methyl-2-oxopentanamido]-9,14,17-trioxo-N-[1(Z)-propenyl]-8,13,16-triazatetracyclo[18.3.1.0(2,7).0(6,10)]tetracosa-1(24),2,4,6,20,22-hexaene-12-carboxamide

There total 69 articles about (10S,11R,12S,15S,18S)-15-(Carbamoylmethyl)-10,11,23-trihydroxy-18-[3(R)-methyl-2-oxopentanamido]-9,14,17-trioxo-N-[1(Z)-propenyl]-8,13,16-triazatetracyclo[18.3.1.0(2,7).0(6,10)]tetracosa-1(24),2,4,6,20,22-hexaene-12-carboxamide 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:

7-iodooxindole (31676-49-0) → TMC-95A (262854-05-7,220666-21-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: LDA / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: 45 percent / Et₃N; MsCl / CH₂Cl₂ / 1.33 h / -75 - -50 °C

2.1: 65 percent / K₂CO₃; [PdCl₂(dppf)]*CH₂Cl₂ / 1,2-dimethoxy-ethane / 5 h / 80 °C

3.1: aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

4.1: 85 percent / 1-hydroxy-7-azabenzotriazole; 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 2.5 h / 20 °C

5.1: OsO₄; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / 2-methyl-propan-2-ol; H₂O / 14 h / 20 °C

6.1: pyridinum p-toluene sulfonate / methanol / 4 h / 70 °C

7.1: 287 mg / imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 2.5 h / 20 °C

8.1: TFA / CH₂Cl₂ / 1.67 h / 20 °C

9.1: 18 mg / N,N-diisopropylethylamine; 1-hydroxy-7-azabenzotriazole; 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride / CH₂Cl₂; dimethylformamide / 4 h / 20 °C

10.1: H₂ / Pd/C / ethanol / 19 h / 20 °C

11.1: 11.9 mg / 1-hydroxy-7-azabenzotriazole; 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride / dimethylformamide; CH₂Cl₂ / 1.5 h / 20 °C

12.1: HF; pyridine / tetrahydrofuran / 22 h / 20 °C

12.2: TMSOMe / tetrahydrofuran / 0.5 h

13.1: 2,6-lutidine / 24 h / 20 °C

13.2: 6.6 mg / aq. citric acid / ethyl acetate / 0.5 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; lithium hydroxide; osmium(VIII) oxide; 1-hydroxy-7-aza-benzotriazole; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; potassium carbonate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Suzuki coupling;

DOI:10.1021/ja049821k

Reference yield:

L-Tyr-OMe (1080-06-4) → TMC-95A (262854-05-7,220666-21-7)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 100 percent / Na₂CO₃ / acetone; H₂O / 2 h / 20 °C

2.1: 100 percent / CsCO₃ / acetone / 4 h

3.1: 100 percent / I₂; Ag₂SO₄ / methanol / 2 h / 20 °C

4.1: 91 percent / KOAc; [PdCl(dppf)]*CH₂Cl₂ / 1,2-dimethoxy-ethane / 12 h / 80 °C

5.1: 65 percent / K₂CO₃; [PdCl₂(dppf)]*CH₂Cl₂ / 1,2-dimethoxy-ethane / 5 h / 80 °C

6.1: aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

7.1: 85 percent / 1-hydroxy-7-azabenzotriazole; 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 2.5 h / 20 °C

8.1: OsO₄; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / 2-methyl-propan-2-ol; H₂O / 14 h / 20 °C

9.1: pyridinum p-toluene sulfonate / methanol / 4 h / 70 °C

10.1: 287 mg / imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 2.5 h / 20 °C

11.1: TFA / CH₂Cl₂ / 1.67 h / 20 °C

12.1: 18 mg / N,N-diisopropylethylamine; 1-hydroxy-7-azabenzotriazole; 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride / CH₂Cl₂; dimethylformamide / 4 h / 20 °C

13.1: H₂ / Pd/C / ethanol / 19 h / 20 °C

14.1: 11.9 mg / 1-hydroxy-7-azabenzotriazole; 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride / dimethylformamide; CH₂Cl₂ / 1.5 h / 20 °C

15.1: HF; pyridine / tetrahydrofuran / 22 h / 20 °C

15.2: TMSOMe / tetrahydrofuran / 0.5 h

16.1: 2,6-lutidine / 24 h / 20 °C

16.2: 6.6 mg / aq. citric acid / ethyl acetate / 0.5 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; lithium hydroxide; osmium(VIII) oxide; 1-hydroxy-7-aza-benzotriazole; hydrogen fluoride; hydrogen; iodine; potassium acetate; pyridinium p-toluenesulfonate; sodium carbonate; potassium carbonate; silver sulfate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 5.1: Suzuki coupling;

DOI:10.1021/ja049821k

Reference yield:

N-(benzyloxycarbonyl)-L-tyrosine methyl ester (13512-31-7) → TMC-95A (262854-05-7,220666-21-7)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 100 percent / CsCO₃ / acetone / 4 h

2.1: 100 percent / I₂; Ag₂SO₄ / methanol / 2 h / 20 °C

3.1: 91 percent / KOAc; [PdCl(dppf)]*CH₂Cl₂ / 1,2-dimethoxy-ethane / 12 h / 80 °C

4.1: 65 percent / K₂CO₃; [PdCl₂(dppf)]*CH₂Cl₂ / 1,2-dimethoxy-ethane / 5 h / 80 °C

5.1: aq. LiOH / tetrahydrofuran / 2.5 h / 0 °C

6.1: 85 percent / 1-hydroxy-7-azabenzotriazole; 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 2.5 h / 20 °C

7.1: OsO₄; 4-methylmorpholine N-oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine / 2-methyl-propan-2-ol; H₂O / 14 h / 20 °C

8.1: pyridinum p-toluene sulfonate / methanol / 4 h / 70 °C

9.1: 287 mg / imidazole; 4-dimethylaminopyridine / CH₂Cl₂ / 2.5 h / 20 °C

10.1: TFA / CH₂Cl₂ / 1.67 h / 20 °C

11.1: 18 mg / N,N-diisopropylethylamine; 1-hydroxy-7-azabenzotriazole; 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride / CH₂Cl₂; dimethylformamide / 4 h / 20 °C

12.1: H₂ / Pd/C / ethanol / 19 h / 20 °C

13.1: 11.9 mg / 1-hydroxy-7-azabenzotriazole; 1-[3-dimethylaminopropyl]-3-ethylcarbodiimide hydrochloride / dimethylformamide; CH₂Cl₂ / 1.5 h / 20 °C

14.1: HF; pyridine / tetrahydrofuran / 22 h / 20 °C

14.2: TMSOMe / tetrahydrofuran / 0.5 h

15.1: 2,6-lutidine / 24 h / 20 °C

15.2: 6.6 mg / aq. citric acid / ethyl acetate / 0.5 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; lithium hydroxide; osmium(VIII) oxide; 1-hydroxy-7-aza-benzotriazole; hydrogen fluoride; hydrogen; iodine; potassium acetate; pyridinium p-toluenesulfonate; potassium carbonate; silver sulfate; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 4.1: Suzuki coupling;

DOI:10.1021/ja049821k

upstream raw materials:

N-1-triethylsilylprop-2-en-1-ylamine

7-iodooxindole

L-Tyr-OMe

N-(benzyloxycarbonyl)-L-tyrosine methyl ester