{5-(4-benzoyl-phenyl)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[3-methyl-1-(1-{5-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentylcarbamoyl}-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-pentyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {5-(4-benzoyl-phenyl)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[3-methyl-1-(1-{5-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentylcarbamoyl}-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-pentyl}-carbamic acid tert-butyl ester
• CAS No.: 794525-93-2
• Molecular Formula: C₆₇H₉₅N₇O₉SSi
• Molecular Weight: 1202.68

Synonyms:{5-(4-benzoyl-phenyl)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[3-methyl-1-(1-{5-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentylcarbamoyl}-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-pentyl}-carbamic acid tert-butyl ester

Chemical Property of {5-(4-benzoyl-phenyl)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[3-methyl-1-(1-{5-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentylcarbamoyl}-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-pentyl}-carbamic acid tert-butyl ester

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Technology Process of {5-(4-benzoyl-phenyl)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[3-methyl-1-(1-{5-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentylcarbamoyl}-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-pentyl}-carbamic acid tert-butyl ester

There total 15 articles about {5-(4-benzoyl-phenyl)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[3-methyl-1-(1-{5-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentylcarbamoyl}-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-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:

(4-bromophenyl)(phenyl)methanone (90-90-4) → {5-(4-benzoyl-phenyl)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[3-methyl-1-(1-{5-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentylcarbamoyl}-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-pentyl}-carbamic acid tert-butyl ester (794525-93-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 92 percent / p-TsOH / benzene / 44 h / Heating

2.1: 95 percent / n-BuLi / tetrahydrofuran / -78 °C

3.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

3.2: tetrahydrofuran / 0.5 h / -78 °C

3.3: 80 percent / Ac₂O; Et₃N / 1 h / 120 °C

4.1: 90 percent / H₂ / PtO₂ / ethyl acetate / 2 h / 20 °C

5.1: TFA / 20 °C

6.1: 108 mg / Et₃N / CHCl₃; dimethylformamide; H₂O / 3 h / 20 °C

7.1: aq. LiOH / 1,2-dimethoxy-ethane / 5 h / 20 °C

8.1: imidazole / dimethylformamide / 20 °C

8.2: 129 mg / MeOH / dimethylformamide / 2 h

9.1: 82 percent / 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 20 °C

With 1H-imidazole; lithium hydroxide; n-butyllithium; hydrogen; benzotriazol-1-ol; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; 1,2-dimethoxyethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo0486948

Reference yield:

(4R)-4-{1-[(S)-(tert-butoxycarbonyl)amino]-2-phenylethyl}-γ-butyrolactone (135130-98-2) → {5-(4-benzoyl-phenyl)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[3-methyl-1-(1-{5-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentylcarbamoyl}-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-pentyl}-carbamic acid tert-butyl ester (794525-93-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran / 0.5 h / -78 °C

1.3: 80 percent / Ac₂O; Et₃N / 1 h / 120 °C

2.1: 90 percent / H₂ / PtO₂ / ethyl acetate / 2 h / 20 °C

3.1: TFA / 20 °C

4.1: 108 mg / Et₃N / CHCl₃; dimethylformamide; H₂O / 3 h / 20 °C

5.1: aq. LiOH / 1,2-dimethoxy-ethane / 5 h / 20 °C

6.1: imidazole / dimethylformamide / 20 °C

6.2: 129 mg / MeOH / dimethylformamide / 2 h

7.1: 82 percent / 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 20 °C

With 1H-imidazole; lithium hydroxide; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; 1,2-dimethoxyethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo0486948

Reference yield:

2-(4-bromophenyl)-2-phenyl-1,3-dioxolane (59793-76-9) → {5-(4-benzoyl-phenyl)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-4-[3-methyl-1-(1-{5-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-pentylcarbamoyl}-2-phenyl-ethylcarbamoyl)-butylcarbamoyl]-pentyl}-carbamic acid tert-butyl ester (794525-93-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 95 percent / n-BuLi / tetrahydrofuran / -78 °C

2.1: LDA / tetrahydrofuran / 0.5 h / -78 °C

2.2: tetrahydrofuran / 0.5 h / -78 °C

2.3: 80 percent / Ac₂O; Et₃N / 1 h / 120 °C

3.1: 90 percent / H₂ / PtO₂ / ethyl acetate / 2 h / 20 °C

4.1: TFA / 20 °C

5.1: 108 mg / Et₃N / CHCl₃; dimethylformamide; H₂O / 3 h / 20 °C

6.1: aq. LiOH / 1,2-dimethoxy-ethane / 5 h / 20 °C

7.1: imidazole / dimethylformamide / 20 °C

7.2: 129 mg / MeOH / dimethylformamide / 2 h

8.1: 82 percent / 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 20 °C

With 1H-imidazole; lithium hydroxide; n-butyllithium; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; 1,2-dimethoxyethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo0486948

upstream raw materials:

(4-bromophenyl)(phenyl)methanone

di-tert-butyl dicarbonate

N-[N-(tert-butoxycarbonyl)-L-leucyl]-L-phenylalanine

(4R)-4-{1-[(S)-(tert-butoxycarbonyl)amino]-2-phenylethyl}-γ-butyrolactone

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