{(1S,2R,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {(1S,2R,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester
• CAS No.: 338801-69-7
• Molecular Formula: C₄₅H₆₆N₄O₆Si
• Molecular Weight: 787.128

Synonyms:{(1S,2R,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester

Chemical Property of {(1S,2R,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester

Chemical Property:

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Technology Process of {(1S,2R,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester

There total 21 articles about {(1S,2R,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester 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: 91.0%

leucylphenylalanylamide (38678-60-3) + (2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-6-phenylhexanoic acid (98818-49-6) → {(1S,2R,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester (338801-69-7)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/S0040-4020(00)01167-4

Reference yield:

(4R)-4-{1-[(S)-(tert-butoxycarbonyl)amino]-2-phenylethyl}-γ-butyrolactone (135130-98-2) → {(1S,2R,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester (338801-69-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium diisopropylamide / hexane; tetrahydrofuran / 0.67 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 °C

1.3: Ac₂O; Et₃N / 1 h / 120 °C

2.1: H₂ / Pd/C / ethyl acetate; methanol / 2 h / 2585.74 Torr

3.1: 3.6 g / LiOH; water; DME / 5 h / 20 °C

4.1: 3.4 g / imidazole; DMF

5.1: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; DMF / 20 °C

With 1H-imidazole; lithium hydroxide; 1,2-dimethoxyethane; water; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; ethyl acetate;

DOI:10.1016/S0040-4020(00)01167-4

Reference yield:

benzaldehyde (100-52-7) → {(1S,2R,4R)-1-Benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-5-phenyl-pentyl}-carbamic acid tert-butyl ester (338801-69-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium diisopropylamide / hexane; tetrahydrofuran / 0.67 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 °C

1.3: Ac₂O; Et₃N / 1 h / 120 °C

2.1: H₂ / Pd/C / ethyl acetate; methanol / 2 h / 2585.74 Torr

3.1: 3.6 g / LiOH; water; DME / 5 h / 20 °C

4.1: 3.4 g / imidazole; DMF

5.1: 91 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole; DMF / 20 °C

With 1H-imidazole; lithium hydroxide; 1,2-dimethoxyethane; water; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N,N-dimethyl-formamide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; ethyl acetate;

DOI:10.1016/S0040-4020(00)01167-4

upstream raw materials:

leucylphenylalanylamide

(2R,4R,5S)-2-benzyl-5-tert-butoxycarbonylamino-4-(tert-butyldimethylsilyloxy)-6-phenylhexanoic acid

N-tert-butoxycarbonyl-L-leucine

L-Phenylalanine amide

Downstream raw materials:

(5S)-(tert-butoxycarbonylamino)-6-phenyl-(4R)-hydroxy-(2R)-benzylhexanoyl-L-leucy-L-phenylalaninamide

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