(2R)-2-((2S)-2-Hydroxy-3-tritylsulfanylpropyl)nonanoic acid ((1S)-2,2-dimethyl-1-methylcarbamoylpropyl)amide

Base Information

• Chemical Name: (2R)-2-((2S)-2-Hydroxy-3-tritylsulfanylpropyl)nonanoic acid ((1S)-2,2-dimethyl-1-methylcarbamoylpropyl)amide
• CAS No.: 202345-10-6
• Molecular Formula: C₃₈H₅₂N₂O₃S
• Molecular Weight: 616.908

Synonyms:(2R)-2-((2S)-2-Hydroxy-3-tritylsulfanylpropyl)nonanoic acid ((1S)-2,2-dimethyl-1-methylcarbamoylpropyl)amide

Chemical Property of (2R)-2-((2S)-2-Hydroxy-3-tritylsulfanylpropyl)nonanoic acid ((1S)-2,2-dimethyl-1-methylcarbamoylpropyl)amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (2R)-2-((2S)-2-Hydroxy-3-tritylsulfanylpropyl)nonanoic acid ((1S)-2,2-dimethyl-1-methylcarbamoylpropyl)amide

There total 9 articles about (2R)-2-((2S)-2-Hydroxy-3-tritylsulfanylpropyl)nonanoic acid ((1S)-2,2-dimethyl-1-methylcarbamoylpropyl)amide 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: 45.0%

2-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-tritylsulfanyl-propyl]-nonanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide (249588-55-4) → (S)-2-((S)-2-Hydroxy-3-tritylsulfanyl-propyl)-nonanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide (249588-57-6) + (2R)-2-((2S)-2-Hydroxy-3-tritylsulfanylpropyl)nonanoic acid ((1S)-2,2-dimethyl-1-methylcarbamoylpropyl)amide (202345-10-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1055/s-1999-2858

Reference yield:

triphenylmethanethiol (3695-77-0) → (2R)-2-((2S)-2-Hydroxy-3-tritylsulfanylpropyl)nonanoic acid ((1S)-2,2-dimethyl-1-methylcarbamoylpropyl)amide (202345-10-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 63 percent / KF / methanol / 36 h / 20 °C

2.1: 88 percent / imidazole; DMAP / CH₂Cl₂ / 12 h / 20 °C

3.1: NaH / dimethylformamide / 1 h / 20 °C

3.2: 53 percent / TBAI; imidazole / dimethylformamide / 18 h / 80 °C

4.1: NaH / dimethylformamide / 0.5 h / 20 °C

4.2: 91 percent / KI / dimethylformamide / 12 h / 50 °C

5.1: morpholine / (Ph₃P)4Pd / tetrahydrofuran / 3 h / 20 °C

6.1: dioxane / 3 h / Heating

7.1: 90 percent / EDC; HOBt; DIEA / CH₂Cl₂ / 12 h / 20 °C

8.1: 39 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

With morpholine; 1H-imidazole; dmap; potassium fluoride; tetrabutyl ammonium fluoride; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Substitution / 3.1: Metallation / 3.2: Alkylation / 4.1: Metallation / 4.2: Alkylation / 5.1: Substitution / 6.1: Decarboxylation / 7.1: Acylation / 8.1: Desilylation;

DOI:10.1055/s-1999-2858

Reference yield:

Toluene-4-sulfonic acid (S)-2-hydroxy-3-tritylsulfanyl-propyl ester (249588-46-3) → (2R)-2-((2S)-2-Hydroxy-3-tritylsulfanylpropyl)nonanoic acid ((1S)-2,2-dimethyl-1-methylcarbamoylpropyl)amide (202345-10-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 88 percent / imidazole; DMAP / CH₂Cl₂ / 12 h / 20 °C

2.1: NaH / dimethylformamide / 1 h / 20 °C

2.2: 53 percent / TBAI; imidazole / dimethylformamide / 18 h / 80 °C

3.1: NaH / dimethylformamide / 0.5 h / 20 °C

3.2: 91 percent / KI / dimethylformamide / 12 h / 50 °C

4.1: morpholine / (Ph₃P)4Pd / tetrahydrofuran / 3 h / 20 °C

5.1: dioxane / 3 h / Heating

6.1: 90 percent / EDC; HOBt; DIEA / CH₂Cl₂ / 12 h / 20 °C

7.1: 39 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

With morpholine; 1H-imidazole; dmap; tetrabutyl ammonium fluoride; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Metallation / 2.2: Alkylation / 3.1: Metallation / 3.2: Alkylation / 4.1: Substitution / 5.1: Decarboxylation / 6.1: Acylation / 7.1: Desilylation;

DOI:10.1055/s-1999-2858

upstream raw materials:

2-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-tritylsulfanyl-propyl]-nonanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide

triphenylmethanethiol

Toluene-4-sulfonic acid (S)-2-hydroxy-3-tritylsulfanyl-propyl ester

toluene-4-sulfonic acid 2-(tert-butyl-dimethyl-silanyloxy)-3-tritylsulfanyl-propyl ester

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