(R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid

Base Information

• Chemical Name: (R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid
• CAS No.: 320748-88-7
• Molecular Formula: C₃₀H₅₅NO₅Si₂
• Molecular Weight: 565.941
• Mol file: 320748-88-7.mol

Synonyms:(R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid

Chemical Property of (R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid

There total 9 articles about (R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic 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: 95.0%

(R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid benzyl ester (320748-87-6) → (R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid (320748-88-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 2h; under 760.051 Torr;

DOI:10.1021/ol006759x

Reference yield:

4-bromo-phenol (106-41-2) → (R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid (320748-88-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 88 percent / imidazole / tetrahydrofuran / 36 h / 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane / 0.17 h / -78 °C

2.2: 83 percent / CuBr*SMe₂; BF₃*OEt₂ / tetrahydrofuran; pentane / -45 - -20 °C

3.1: imidazole / CH₂Cl₂ / 11 h / 20 °C

4.1: 289 mg / H₂ / Pd/C / ethyl acetate / 50 h / 2280.15 Torr

5.1: 84 percent / Dess-Martin periodinone / CH₂Cl₂ / 0.75 h / 0 °C

6.1: 93 percent / NaClO₂; NaH₂PO₄*H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h / 0 °C

7.1: diethyl cyanophosphinate; iPr₂NEt / CH₂Cl₂ / 0.33 h / -20 °C

7.2: 68 percent / CH₂Cl₂ / 2 h / -20 °C

8.1: 95 percent / H₂ / Pd/C / ethanol / 2 h / 760.05 Torr

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; diethylphosphoryl cyanide; 2-methyl-but-2-ene; hydrogen; tert.-butyl lithium; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol; pentane; 5.1: Dess-Martin oxidation;

DOI:10.1021/ol006759x

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid (320748-88-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 88 percent / imidazole / tetrahydrofuran / 36 h / 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane / 0.17 h / -78 °C

2.2: 83 percent / CuBr*SMe₂; BF₃*OEt₂ / tetrahydrofuran; pentane / -45 - -20 °C

3.1: imidazole / CH₂Cl₂ / 11 h / 20 °C

4.1: 289 mg / H₂ / Pd/C / ethyl acetate / 50 h / 2280.15 Torr

5.1: 84 percent / Dess-Martin periodinone / CH₂Cl₂ / 0.75 h / 0 °C

6.1: 93 percent / NaClO₂; NaH₂PO₄*H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 1 h / 0 °C

7.1: diethyl cyanophosphinate; iPr₂NEt / CH₂Cl₂ / 0.33 h / -20 °C

7.2: 68 percent / CH₂Cl₂ / 2 h / -20 °C

8.1: 95 percent / H₂ / Pd/C / ethanol / 2 h / 760.05 Torr

With 1H-imidazole; sodium chlorite; sodium dihydrogenphosphate; diethylphosphoryl cyanide; 2-methyl-but-2-ene; hydrogen; tert.-butyl lithium; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol; pentane; 5.1: Dess-Martin oxidation;

DOI:10.1021/ol006759x

upstream raw materials:

(R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid benzyl ester

4-bromo-phenol

triisopropylsilyl chloride

4-bromo-1-(triisopropylsilyloxy)benzene

Downstream raw materials:

C₇₃H₁₂₂N₆O₁₁Si₄