2-((4S,13S)-13-Benzyloxycarbonylamino-2,10-dioxo-15-thia-3,9,17-triaza-bicyclo[12.2.1]heptadeca-1⁽¹⁶⁾,14⁽¹⁷⁾-dien-4-yl)-oxazole-4-carboxylic acid

Base Information

• Chemical Name: 2-((4S,13S)-13-Benzyloxycarbonylamino-2,10-dioxo-15-thia-3,9,17-triaza-bicyclo[12.2.1]heptadeca-1⁽¹⁶⁾,14⁽¹⁷⁾-dien-4-yl)-oxazole-4-carboxylic acid
• CAS No.: 474686-27-6
• Molecular Formula: C₂₅H₂₇N₅O₇S
• Molecular Weight: 541.585

Synonyms:2-((4S,13S)-13-Benzyloxycarbonylamino-2,10-dioxo-15-thia-3,9,17-triaza-bicyclo[12.2.1]heptadeca-1⁽¹⁶⁾,14⁽¹⁷⁾-dien-4-yl)-oxazole-4-carboxylic acid

Chemical Property of 2-((4S,13S)-13-Benzyloxycarbonylamino-2,10-dioxo-15-thia-3,9,17-triaza-bicyclo[12.2.1]heptadeca-1⁽¹⁶⁾,14⁽¹⁷⁾-dien-4-yl)-oxazole-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((4S,13S)-13-Benzyloxycarbonylamino-2,10-dioxo-15-thia-3,9,17-triaza-bicyclo[12.2.1]heptadeca-1⁽¹⁶⁾,14⁽¹⁷⁾-dien-4-yl)-oxazole-4-carboxylic acid

There total 9 articles about 2-((4S,13S)-13-Benzyloxycarbonylamino-2,10-dioxo-15-thia-3,9,17-triaza-bicyclo[12.2.1]heptadeca-1⁽¹⁶⁾,14⁽¹⁷⁾-dien-4-yl)-oxazole-4-carboxylic acid 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: 72.0%

2-((4S,13S)-13-Benzyloxycarbonylamino-2,10-dioxo-15-thia-3,9,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-oxazole-4-carboxylic acid methyl ester → 2-((4S,13S)-13-Benzyloxycarbonylamino-2,10-dioxo-15-thia-3,9,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-oxazole-4-carboxylic acid (474686-27-6)

Guidance literature:

With lithium hydroxide; In ethanol; water; at 2 ℃; for 3h;

DOI:10.1021/ol026463m

Reference yield:

(S)-2-((S)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-hexanoylamino)-3-hydroxy-propionic acid methyl ester (84860-21-9) → 2-((4S,13S)-13-Benzyloxycarbonylamino-2,10-dioxo-15-thia-3,9,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-oxazole-4-carboxylic acid (474686-27-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: [bis(2-methoxyethyl)amino]-sulfur trifluoride / CH₂Cl₂ / 4 h / -30 °C

1.2: 89 percent / bromotrichloromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene / -40 - -5 °C

2.1: 100 percent / H₂ / palladium on carbone / methanol; ethyl acetate / 0.5 h / 20 °C / 1810.07 Torr

3.1: 99 percent / benzotriazol-1-yl-oxy-tris(dimethylamino) phosphonium PF₆; diisopropylethylamine / dimethylformamide / 18 h / 20 °C

4.1: 100 percent / CH₂Cl₂ / 2 h / 20 °C

5.1: benzotriazol-1-yl-oxy-tris-(dimethylamino) phosphonium PF₆; diisopropylethyl amine / dimethylformamide / 22 h / 20 °C

6.1: 72 percent / LiOH*H₂O / ethanol; H₂O / 3 h / 2 °C

With lithium hydroxide; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; (bis-(2-methoxyethyl)amino)sulfur trufluoride; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ol026463m

Reference yield:

2-(1-benzyloxycarbonylamino-5-tert-butoxycarbonylamino-pentyl)-oxazole-4-carboxylic acid methyl ester (474686-33-4) → 2-((4S,13S)-13-Benzyloxycarbonylamino-2,10-dioxo-15-thia-3,9,17-triaza-bicyclo[12.2.1]heptadeca-1(16),14(17)-dien-4-yl)-oxazole-4-carboxylic acid (474686-27-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / H₂ / palladium on carbone / methanol; ethyl acetate / 0.5 h / 20 °C / 1810.07 Torr

2: 99 percent / benzotriazol-1-yl-oxy-tris(dimethylamino) phosphonium PF₆; diisopropylethylamine / dimethylformamide / 18 h / 20 °C

3: 100 percent / CH₂Cl₂ / 2 h / 20 °C

4: benzotriazol-1-yl-oxy-tris-(dimethylamino) phosphonium PF₆; diisopropylethyl amine / dimethylformamide / 22 h / 20 °C

5: 72 percent / LiOH*H₂O / ethanol; H₂O / 3 h / 2 °C

With lithium hydroxide; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ol026463m

upstream raw materials:

2-(1-benzyloxycarbonylamino-3-tert-butoxycarbonyl-propyl)-thiazole-4-carboxylic acid ethyl ester

2-(1-benzyloxycarbonylamino-5-tert-butoxycarbonylamino-pentyl)-oxazole-4-carboxylic acid methyl ester

(S)-2-((S)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-hexanoylamino)-3-hydroxy-propionic acid methyl ester

Z-Lys(Boc)-OH

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