tert-butyl (S)-(1-((R)-4-(2-phenyl-1,3-dioxolan-2-yl)benzylidene)-tetrahydro-5-oxofuran-2-yl)-2-phenylethylcarbamate

Base Information

• Chemical Name: tert-butyl (S)-(1-((R)-4-(2-phenyl-1,3-dioxolan-2-yl)benzylidene)-tetrahydro-5-oxofuran-2-yl)-2-phenylethylcarbamate
• CAS No.: 794525-84-1
• Molecular Formula: C₃₃H₃₅NO₆
• Molecular Weight: 541.644
• Mol file: 794525-84-1.mol

Synonyms:tert-butyl (S)-(1-((R)-4-(2-phenyl-1,3-dioxolan-2-yl)benzylidene)-tetrahydro-5-oxofuran-2-yl)-2-phenylethylcarbamate

Chemical Property of tert-butyl (S)-(1-((R)-4-(2-phenyl-1,3-dioxolan-2-yl)benzylidene)-tetrahydro-5-oxofuran-2-yl)-2-phenylethylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (S)-(1-((R)-4-(2-phenyl-1,3-dioxolan-2-yl)benzylidene)-tetrahydro-5-oxofuran-2-yl)-2-phenylethylcarbamate

There total 9 articles about tert-butyl (S)-(1-((R)-4-(2-phenyl-1,3-dioxolan-2-yl)benzylidene)-tetrahydro-5-oxofuran-2-yl)-2-phenylethylcarbamate 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: 80.0%

(4R)-4-{1-[(S)-(tert-butoxycarbonyl)amino]-2-phenylethyl}-γ-butyrolactone (135130-98-2) + 4-(2-phenyl-1,3-dioxolan-2-yl)benzaldehyde (41418-67-1) → tert-butyl (S)-(1-((R)-4-(2-phenyl-1,3-dioxolan-2-yl)benzylidene)-tetrahydro-5-oxofuran-2-yl)-2-phenylethylcarbamate (794525-84-1)

Guidance literature:

(4R)-4-{1-[(S)-(tert-butoxycarbonyl)amino]-2-phenylethyl}-γ-butyrolactone; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

4-(2-phenyl-1,3-dioxolan-2-yl)benzaldehyde; In tetrahydrofuran; at -78 ℃; for 0.5h;

With acetic anhydride; triethylamine; at 120 ℃; for 1h;

DOI:10.1021/jo0486948

Reference yield:

(4-bromophenyl)(phenyl)methanone (90-90-4) → tert-butyl (S)-(1-((R)-4-(2-phenyl-1,3-dioxolan-2-yl)benzylidene)-tetrahydro-5-oxofuran-2-yl)-2-phenylethylcarbamate (794525-84-1)

Guidance literature:

Multi-step reaction with 3 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

With n-butyllithium; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; benzene;

DOI:10.1021/jo0486948

Reference yield:

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester (51987-73-6) → tert-butyl (S)-(1-((R)-4-(2-phenyl-1,3-dioxolan-2-yl)benzylidene)-tetrahydro-5-oxofuran-2-yl)-2-phenylethylcarbamate (794525-84-1)

Guidance literature:

Multi-step reaction with 7 steps

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

2.1: 7.8 g / NaBH₄ / toluene; ethanol / 8 h / -78 - 0 °C

3.1: 89 percent / KOH / ethanol / 2 h / 20 °C

4.1: 90 percent / EtONa / ethanol / 20 °C

5.1: LiOH / dimethylformamide; H₂O / 6 h / 50 °C

6.1: toluene / 5 h / Heating

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

7.2: tetrahydrofuran / 0.5 h / -78 °C

7.3: 80 percent / Ac₂O; Et₃N / 1 h / 120 °C

With potassium hydroxide; lithium hydroxide; sodium tetrahydroborate; sodium ethanolate; lithium diisopropyl amide; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo0486948

upstream raw materials:

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

4-(2-phenyl-1,3-dioxolan-2-yl)benzaldehyde

(4-bromophenyl)(phenyl)methanone

(S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester

Downstream raw materials:

tert-butyl (S)-(1-((2R,4R)-4-(2-phenyl-1,3-dioxolan-2-yl)benzyl)-tetrahydro-5-oxofuran-2-yl)-2-phenylethylcarbamate

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

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

(2R,4R,5S)-5-tert-Butoxycarbonylamino-4-hydroxy-6-phenyl-2-[4-(2-phenyl-[1,3]dioxolan-2-yl)-benzyl]-hexanoic acid