(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-isobutyl-5-tritylsulfanyl-pentanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide

Base Information

Chemical Name:(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-isobutyl-5-tritylsulfanyl-pentanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide
CAS No.:249588-54-3
Molecular Formula:C₄₁H₆₀N₂O₃SSi
Molecular Weight:689.091
Hs Code.:

Synonyms:(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-isobutyl-5-tritylsulfanyl-pentanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide

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Chemical Property of (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-isobutyl-5-tritylsulfanyl-pentanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide

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Technology Process of (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-isobutyl-5-tritylsulfanyl-pentanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide

There total 7 articles about (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-isobutyl-5-tritylsulfanyl-pentanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-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%

: 89226-12-0
(S)-2-amino-N,3,3-trimethylbutanamide

: 249588-52-1
4-(tert-butyl-dimethyl-silanyloxy)-2-isobutyl-5-tritylsulfanyl-pentanoic acid

: 249588-54-3
(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-isobutyl-5-tritylsulfanyl-pentanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide

: 202345-08-2
(2R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-isobutyl-5-tritylsulfanyl-pentanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1055/s-1999-2858

Reference yield:

: 3695-77-0
triphenylmethanethiol

: 249588-54-3
(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-isobutyl-5-tritylsulfanyl-pentanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide

Guidance literature:: Multi-step reaction with 7 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: 89 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: 45 percent / EDC; HOBt; DIEA / CH₂Cl₂ / 12 h / 20 °C

With morpholine; 1H-imidazole; dmap; potassium 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;
DOI:10.1055/s-1999-2858

Reference yield:

: 249588-46-3
Toluene-4-sulfonic acid (S)-2-hydroxy-3-tritylsulfanyl-propyl ester

: 249588-54-3
(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-isobutyl-5-tritylsulfanyl-pentanoic acid ((S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-amide

Guidance literature:: Multi-step reaction with 6 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: 89 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: 45 percent / EDC; HOBt; DIEA / CH₂Cl₂ / 12 h / 20 °C

With morpholine; 1H-imidazole; dmap; 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;
DOI:10.1055/s-1999-2858