tert-butyl [(2S,5S,8R,10S,11S,14S,17S)-8,11,14-tribenzyl-2-carbamoyl-10-hydroxy-5-(2-methylpropyl)-4,7,13,16-tetraoxo-1,18-diphenyl-3,6,12,15-tetraazaoctadecan-17-yl]carbamate (non-preferred name)

Base Information

• Chemical Name: tert-butyl [(2S,5S,8R,10S,11S,14S,17S)-8,11,14-tribenzyl-2-carbamoyl-10-hydroxy-5-(2-methylpropyl)-4,7,13,16-tetraoxo-1,18-diphenyl-3,6,12,15-tetraazaoctadecan-17-yl]carbamate (non-preferred name)
• CAS No.: 98818-73-6
• Molecular Formula: C₅₇H₇₀N₆O₈
• Molecular Weight: 967.218

Synonyms:

Chemical Property of tert-butyl [(2S,5S,8R,10S,11S,14S,17S)-8,11,14-tribenzyl-2-carbamoyl-10-hydroxy-5-(2-methylpropyl)-4,7,13,16-tetraoxo-1,18-diphenyl-3,6,12,15-tetraazaoctadecan-17-yl]carbamate (non-preferred name)

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 1205.4°Cat760mmHg
• Flash Point: 682.8°C
• Density: 1.186g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl [(2S,5S,8R,10S,11S,14S,17S)-8,11,14-tribenzyl-2-carbamoyl-10-hydroxy-5-(2-methylpropyl)-4,7,13,16-tetraoxo-1,18-diphenyl-3,6,12,15-tetraazaoctadecan-17-yl]carbamate (non-preferred name)

There total 44 articles about tert-butyl [(2S,5S,8R,10S,11S,14S,17S)-8,11,14-tribenzyl-2-carbamoyl-10-hydroxy-5-(2-methylpropyl)-4,7,13,16-tetraoxo-1,18-diphenyl-3,6,12,15-tetraazaoctadecan-17-yl]carbamate (non-preferred name) 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:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → Nα-<5-<α-(t-Boc-amino)-L-phenylalanyl-L-phenylalanyl>amino>-4-hydroxy-6-phenyl-2-(phenylmethyl)hexanoyl>-L-leucyl-L-phenylalanine amide (98818-73-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) HCl(gas), 2.) EDC, HBT, triethylamine / 1.) EtOAc, 0 deg C, 15 min, 2.) DMF, RT, 40 h

2: HCl(gas) / ethyl acetate

3: EDC, HBT, triethylamine / dimethylformamide / 2 h / Ambient temperature

4: 1M aq. NaOH / dioxane / 18 h / Ambient temperature

5: imidazole / dimethylformamide / 72 h

6: aq. AcOH / tetrahydrofuran / 3 h / Ambient temperature

7: 1.2 g / DCC, HBT, triethylamine / CH₂Cl₂ / 120 h / Ambient temperature

8: tetrabutylammonium fluoride / tetrahydrofuran / 40 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium hydroxide; tetrabutyl ammonium fluoride; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00223a037

Reference yield:

benzyl bromide (100-39-0) → Nα-<5-<α-(t-Boc-amino)-L-phenylalanyl-L-phenylalanyl>amino>-4-hydroxy-6-phenyl-2-(phenylmethyl)hexanoyl>-L-leucyl-L-phenylalanine amide (98818-73-6)

Guidance literature:

Multi-step reaction with 16 steps

1: sodium ethoxide / ethanol / 1 h / 50 °C

2: 3.3 g / pH buffer 10. 1N aq. NaOH / dioxane / 3 h

3: 78 percent / 0.5 h / 120 °C

4: 5.9 g / 1M aq. NaOH / dioxane / 0.5 h

5: imidazole / dimethylformamide / 18 h / Ambient temperature

6: aq. acetic acid / tetrahydrofuran / 1.5 h / Ambient temperature

7: HBT, EDC, triethylamine / dimethylformamide / 3 h / Ambient temperature

8: tetrabutylammonium fluoride / tetrahydrofuran / 40 h / Ambient temperature

9: 1.) HCl(gas), 2.) EDC, HBT, triethylamine / 1.) EtOAc, 0 deg C, 15 min, 2.) DMF, RT, 40 h

10: HCl(gas) / ethyl acetate

11: EDC, HBT, triethylamine / dimethylformamide / 2 h / Ambient temperature

12: 1M aq. NaOH / dioxane / 18 h / Ambient temperature

13: imidazole / dimethylformamide / 72 h

14: aq. AcOH / tetrahydrofuran / 3 h / Ambient temperature

15: 1.2 g / DCC, HBT, triethylamine / CH₂Cl₂ / 120 h / Ambient temperature

16: tetrabutylammonium fluoride / tetrahydrofuran / 40 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium hydroxide; pH buffer 10. 1N aq. NaOH; tetrabutyl ammonium fluoride; sodium ethanolate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00223a037

Reference yield:

(5S,1'S)-carbetoxy-5-<1-<<(1',1-dimethylothoxy)carbonyl>amino>-2-phenylmethyl>dihydrofuran-2(3H)-one (193338-94-2) → Nα-<5-<α-(t-Boc-amino)-L-phenylalanyl-L-phenylalanyl>amino>-4-hydroxy-6-phenyl-2-(phenylmethyl)hexanoyl>-L-leucyl-L-phenylalanine amide (98818-73-6)

Guidance literature:

Multi-step reaction with 16 steps

1: sodium ethoxide / ethanol / 1 h / 50 °C

2: 3.3 g / pH buffer 10. 1N aq. NaOH / dioxane / 3 h

3: 78 percent / 0.5 h / 120 °C

4: 5.9 g / 1M aq. NaOH / dioxane / 0.5 h

5: imidazole / dimethylformamide / 18 h / Ambient temperature

6: aq. acetic acid / tetrahydrofuran / 1.5 h / Ambient temperature

7: HBT, EDC, triethylamine / dimethylformamide / 3 h / Ambient temperature

8: tetrabutylammonium fluoride / tetrahydrofuran / 40 h / Ambient temperature

9: 1.) HCl(gas), 2.) EDC, HBT, triethylamine / 1.) EtOAc, 0 deg C, 15 min, 2.) DMF, RT, 40 h

10: HCl(gas) / ethyl acetate

11: EDC, HBT, triethylamine / dimethylformamide / 2 h / Ambient temperature

12: 1M aq. NaOH / dioxane / 18 h / Ambient temperature

13: imidazole / dimethylformamide / 72 h

14: aq. AcOH / tetrahydrofuran / 3 h / Ambient temperature

15: 1.2 g / DCC, HBT, triethylamine / CH₂Cl₂ / 120 h / Ambient temperature

16: tetrabutylammonium fluoride / tetrahydrofuran / 40 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium hydroxide; pH buffer 10. 1N aq. NaOH; tetrabutyl ammonium fluoride; sodium ethanolate; benzotriazol-1-ol; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00223a037

upstream raw materials:

Boc-Phe-Phe-OH

(2R,4S,5S)-5-Amino-2-benzyl-4-hydroxy-6-phenyl-hexanoic acid [(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butyl]-amide

leucylphenylalanylamide

(3R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one

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