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

Base Information

• Chemical Name: (R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid benzyl ester
• CAS No.: 320748-87-6
• Molecular Formula: C₃₇H₆₁NO₅Si₂
• Molecular Weight: 656.066

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

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

Chemical Property:

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

There total 8 articles about (R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid benzyl 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: 68.0%

(R)-benzyl 2-amino-4-methylpentanoate hydrochloride (68838-94-8) + 2-(R)-(tert-butyldimethylsilanoxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionic acid (320748-81-0) → (R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid benzyl ester (320748-87-6)

Guidance literature:

2-(R)-(tert-butyldimethylsilanoxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionic acid; With diethylphosphoryl cyanide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -20 ℃; for 0.333333h;

(R)-benzyl 2-amino-4-methylpentanoate hydrochloride; In dichloromethane; at -20 ℃; for 2h; Further stages.;

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 benzyl ester (320748-87-6)

Guidance literature:

Multi-step reaction with 7 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

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; 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 benzyl ester (320748-87-6)

Guidance literature:

Multi-step reaction with 7 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

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; dichloromethane; water; ethyl acetate; tert-butyl alcohol; pentane; 5.1: Dess-Martin oxidation;

DOI:10.1021/ol006759x

upstream raw materials:

(R)-benzyl 2-amino-4-methylpentanoate hydrochloride

2-(R)-(tert-butyldimethylsilanoxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionic acid

4-bromo-phenol

triisopropylsilyl chloride

Downstream raw materials:

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

C₇₃H₁₂₂N₆O₁₁Si₄

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