L-Phenylalaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-N-[(1R)-1-(2-benzothiazolylcarb onyl)-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-

Base Information

• Chemical Name: L-Phenylalaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-N-[(1R)-1-(2-benzothiazolylcarb onyl)-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-
• CAS No.: 872983-91-0
• Molecular Formula: C46H56N4O6SSi
• Molecular Weight: 821.125
• Mol file: 872983-91-0.mol

Synonyms:

Chemical Property of L-Phenylalaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-N-[(1R)-1-(2-benzothiazolylcarb onyl)-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Phenylalaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-N-[(1R)-1-(2-benzothiazolylcarb onyl)-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]-

There total 7 articles about L-Phenylalaninamide, N-[(1,1-dimethylethoxy)carbonyl]-L-valyl-N-[(1R)-1-(2-benzothiazolylcarb onyl)-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]propyl]- 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: 85.0%

[(1S)-1-((1S)-1-{(1R)-1-[(benzothiazol-2-yl)(hydroxy)methyl]-3-(tert-butyldiphenylsiloxy)propyl}carbamoyl)-2-methylpropyl]carbamic acid tert-butyl ester (872983-25-0) → (1-{1-[1-(benzothiazole-2-carbonyl)-3-(tert-butyl-diphenyl-silanyloxy)-propylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-methyl-propyl)-carbamic acid tert-butyl ester (872983-91-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 2h;

DOI:10.1016/j.bmc.2005.08.019

Reference yield:

tert-butyl N-[(1R)-3-[tert-butyl(diphenyl)silyl]oxy-1-formylpropyl]carbamate (905716-08-7) → (1-{1-[1-(benzothiazole-2-carbonyl)-3-(tert-butyl-diphenyl-silanyloxy)-propylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-methyl-propyl)-carbamic acid tert-butyl ester (872983-91-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran / -78 °C

1.2: 0.175 g / tetrahydrofuran / 3 h / -78 °C

2.1: trifluoroacetic acid / CH₂Cl₂ / 0 °C

3.1: 0.19 g / 1-hydroxy-1H-benzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; triethylamine / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

4.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

With n-butyllithium; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.08.019

Reference yield:

(2R)-2-tert-butoxycarbamoyl-4-(tert-butyldiphenylsiloxy)butyric acid (872983-22-7) → (1-{1-[1-(benzothiazole-2-carbonyl)-3-(tert-butyl-diphenyl-silanyloxy)-propylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-methyl-propyl)-carbamic acid tert-butyl ester (872983-91-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1,1'-carbonyldiimidazole / CH₂Cl₂ / 0.5 h / 0 °C

1.2: 87 percent / triethylamine / CH₂Cl₂ / cooling

2.1: 0.2 g / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

3.1: n-BuLi / tetrahydrofuran / -78 °C

3.2: 0.175 g / tetrahydrofuran / 3 h / -78 °C

4.1: trifluoroacetic acid / CH₂Cl₂ / 0 °C

5.1: 0.19 g / 1-hydroxy-1H-benzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide HCl; triethylamine / CH₂Cl₂; dimethylformamide / 0.5 h / 0 °C

6.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

With lithium aluminium tetrahydride; n-butyllithium; benzotriazol-1-ol; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; 1,1'-carbonyldiimidazole; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2005.08.019

upstream raw materials:

[(1S)-1-((1S)-1-{(1R)-1-[(benzothiazol-2-yl)(hydroxy)methyl]-3-(tert-butyldiphenylsiloxy)propyl}carbamoyl)-2-methylpropyl]carbamic acid tert-butyl ester

tert-butyl N-[(1R)-3-[tert-butyl(diphenyl)silyl]oxy-1-formylpropyl]carbamate

(2R)-2-tert-butoxycarbamoyl-4-(tert-butyldiphenylsiloxy)butyric acid

[3-(tert-butyl-diphenyl-silanyloxy)-1-(methoxy-methyl-carbamoyl)-propyl]-carbamic acid tert-butyl ester

Downstream raw materials:

((S)-1-{(S)-1-[(R)-1-(Benzothiazole-2-carbonyl)-3-hydroxy-propylcarbamoyl]-2-phenyl-ethylcarbamoyl}-2-methyl-propyl)-carbamic acid tert-butyl ester