(1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)carbamic acid tert-butyl ester

Base Information

• Chemical Name: (1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)carbamic acid tert-butyl ester
• CAS No.: 794525-91-0
• Molecular Formula: C₃₁H₃₃NO₅
• Molecular Weight: 499.607
• Mol file: 794525-91-0.mol

Synonyms:(1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)carbamic acid tert-butyl ester

Chemical Property of (1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)carbamic acid tert-butyl ester

There total 9 articles about (1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)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) → (1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)carbamic acid tert-butyl ester (794525-91-0)

Guidance literature:

Multi-step reaction with 6 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

With n-butyllithium; hydrogen; toluene-4-sulfonic acid; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; 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) → (1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)carbamic acid tert-butyl ester (794525-91-0)

Guidance literature:

Multi-step reaction with 4 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

With hydrogen; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; 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) → (1S-(4-(4R-benzoyl-benzyl)-5-oxo-tetrahydrofuran-2-yl)-2R-phenylethyl)carbamic acid tert-butyl ester (794525-91-0)

Guidance literature:

Multi-step reaction with 5 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

With n-butyllithium; hydrogen; triethylamine; trifluoroacetic acid; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; chloroform; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo0486948

upstream raw materials:

di-tert-butyl dicarbonate

(4-bromophenyl)(phenyl)methanone

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

2-(4-bromophenyl)-2-phenyl-1,3-dioxolane

Downstream raw materials:

(2R,4R,5S)-2-(4-Benzoyl-benzyl)-5-tert-butoxycarbonylamino-4-hydroxy-6-phenyl-hexanoic acid

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

(5-(4-benzoyl-phenyl)-1S-benzyl-2R-(tert-butyldimethylsilanyloxy)-4R-(1-(1S-carbamoyl-2-phenyl-ethylcarbamoyl)-3(1S)-methyl-butylcarbamoyl)-pentyl)carbamic acid tert-butyl ester

{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