2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic acid

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Chemical Name:2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic acid
CAS No.:794525-92-1
Molecular Formula:C₃₇H₄₉NO₆Si
Molecular Weight:631.885
Hs Code.:

Synonyms:2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic acid

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Chemical Property of 2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic acid

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Technology Process of 2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic acid

There total 12 articles about 2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic 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:

: 90-90-4
(4-bromophenyl)(phenyl)methanone

: 794525-92-1
2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic acid

Guidance literature:: Multi-step reaction with 8 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

With 1H-imidazole; lithium hydroxide; n-butyllithium; hydrogen; toluene-4-sulfonic acid; 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:

: 135130-98-2
(4R)-4-{1-[(S)-(tert-butoxycarbonyl)amino]-2-phenylethyl}-γ-butyrolactone

: 794525-92-1
2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic acid

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; lithium hydroxide; hydrogen; 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:

: 59793-76-9
2-(4-bromophenyl)-2-phenyl-1,3-dioxolane

: 794525-92-1
2R-(4-benzoyl-benzyl)-5S-tert-butoxycarbonylamino-4R-(tert-butyldimethylsilanyloxy)-6-phenyl-hexanoic acid

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; lithium hydroxide; n-butyllithium; hydrogen; 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