(R)-4-{(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2R,3R)-2-methoxycarbonyl-3-phenyl-cyclopropyl)-methyl]-propylcarbamoyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (R)-4-{(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2R,3R)-2-methoxycarbonyl-3-phenyl-cyclopropyl)-methyl]-propylcarbamoyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 331821-68-2
• Molecular Formula: C₃₂H₅₂N₂O₆SSi
• Molecular Weight: 620.926

Synonyms:(R)-4-{(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2R,3R)-2-methoxycarbonyl-3-phenyl-cyclopropyl)-methyl]-propylcarbamoyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (R)-4-{(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2R,3R)-2-methoxycarbonyl-3-phenyl-cyclopropyl)-methyl]-propylcarbamoyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (R)-4-{(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2R,3R)-2-methoxycarbonyl-3-phenyl-cyclopropyl)-methyl]-propylcarbamoyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

There total 19 articles about (R)-4-{(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2R,3R)-2-methoxycarbonyl-3-phenyl-cyclopropyl)-methyl]-propylcarbamoyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl 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:

phenylacetylene (536-74-3) → (R)-4-{(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2R,3R)-2-methoxycarbonyl-3-phenyl-cyclopropyl)-methyl]-propylcarbamoyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester (331821-68-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: n-BuLi; 18-crown-6 / tetrahydrofuran; hexane / 1.17 h / -78 °C

1.2: 76 percent / tetrahydrofuran; hexane / 2.25 h / -78 °C

2.1: 87 percent / H₂; ethylenediamine / P-2 Ni / ethanol

3.1: N,N-dimethylaniline / CH₂Cl₂ / 0.25 h / 0 °C

4.1: 516 mg / Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

5.1: Cu(TBS)2 / toluene / Heating

6.1: aq. HCl; triethylsilane / dioxane / 1 h

7.1: Et₃N / acetonitrile / 12 h / 20 °C

8.1: 95 percent / DEAD; PPh₃ / tetrahydrofuran / 3.5 h / 20 °C

9.1: CuBr*DMS / diethyl ether / 0 °C

9.2: 93 percent / diethyl ether; CH₂Cl₂ / 0.17 h / 0 - 20 °C

10.1: HCl / dioxane / 0.5 h / Heating

11.1: Et₃N; HOBt; DCC / CH₂Cl₂; dimethylformamide / 3 h / 0 °C

12.1: aq. NaOH / ethanol / 1 h

13.1: methanol; diethyl ether

14.1: 2,6-lutidine / CH₂Cl₂ / 2 h / -78 - -20 °C

With 2,6-dimethylpyridine; hydrogenchloride; triethylsilane; sodium hydroxide; n-butyllithium; copper(I) bromide dimethylsulfide complex; 18-crown-6 ether; hydrogen; benzotriazol-1-ol; N,N-dimethyl-aniline; ethylenediamine; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; Cu(TBS)2; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 8.1: Mitsunobu cyclization;

DOI:10.1021/jo001257i

Reference yield:

lithium phenylacetylide (4440-01-1) → (R)-4-{(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2R,3R)-2-methoxycarbonyl-3-phenyl-cyclopropyl)-methyl]-propylcarbamoyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester (331821-68-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 13 percent / ZnBr₂ / diethyl ether / -78 - 20 °C

2.1: 87 percent / H₂; ethylenediamine / P-2 Ni / ethanol

3.1: N,N-dimethylaniline / CH₂Cl₂ / 0.25 h / 0 °C

4.1: 516 mg / Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

5.1: Cu(TBS)2 / toluene / Heating

6.1: aq. HCl; triethylsilane / dioxane / 1 h

7.1: Et₃N / acetonitrile / 12 h / 20 °C

8.1: 95 percent / DEAD; PPh₃ / tetrahydrofuran / 3.5 h / 20 °C

9.1: CuBr*DMS / diethyl ether / 0 °C

9.2: 93 percent / diethyl ether; CH₂Cl₂ / 0.17 h / 0 - 20 °C

10.1: HCl / dioxane / 0.5 h / Heating

11.1: Et₃N; HOBt; DCC / CH₂Cl₂; dimethylformamide / 3 h / 0 °C

12.1: aq. NaOH / ethanol / 1 h

13.1: methanol; diethyl ether

14.1: 2,6-lutidine / CH₂Cl₂ / 2 h / -78 - -20 °C

With 2,6-dimethylpyridine; hydrogenchloride; triethylsilane; sodium hydroxide; copper(I) bromide dimethylsulfide complex; hydrogen; benzotriazol-1-ol; N,N-dimethyl-aniline; ethylenediamine; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; zinc dibromide; diethylazodicarboxylate; Cu(TBS)2; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 8.1: Mitsunobu cyclization;

DOI:10.1021/jo001257i

Reference yield:

tert-butyl (4S)-4-<(1R)-1-hydroxy-3-phenyl-2-propynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (241478-33-1) → (R)-4-{(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2R,3R)-2-methoxycarbonyl-3-phenyl-cyclopropyl)-methyl]-propylcarbamoyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester (331821-68-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 87 percent / H₂; ethylenediamine / P-2 Ni / ethanol

2.1: N,N-dimethylaniline / CH₂Cl₂ / 0.25 h / 0 °C

3.1: 516 mg / Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

4.1: Cu(TBS)2 / toluene / Heating

5.1: aq. HCl; triethylsilane / dioxane / 1 h

6.1: Et₃N / acetonitrile / 12 h / 20 °C

7.1: 95 percent / DEAD; PPh₃ / tetrahydrofuran / 3.5 h / 20 °C

8.1: CuBr*DMS / diethyl ether / 0 °C

8.2: 93 percent / diethyl ether; CH₂Cl₂ / 0.17 h / 0 - 20 °C

9.1: HCl / dioxane / 0.5 h / Heating

10.1: Et₃N; HOBt; DCC / CH₂Cl₂; dimethylformamide / 3 h / 0 °C

11.1: aq. NaOH / ethanol / 1 h

12.1: methanol; diethyl ether

13.1: 2,6-lutidine / CH₂Cl₂ / 2 h / -78 - -20 °C

With 2,6-dimethylpyridine; hydrogenchloride; triethylsilane; sodium hydroxide; copper(I) bromide dimethylsulfide complex; hydrogen; benzotriazol-1-ol; N,N-dimethyl-aniline; ethylenediamine; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; Cu(TBS)2; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 7.1: Mitsunobu cyclization;

DOI:10.1021/jo001257i

upstream raw materials:

t-butyldimethylsiyl triflate

(4R)-3-(tert-butoxycarbonyl)-2,2-dimethylthiazolidine-4-carboxylic acid

phenylacetylene

tert-butyl (4S)-4-<(1R)-1-hydroxy-3-phenyl-2-propynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Downstream raw materials:

(R)-4-{(S)-1-[(S)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2R,3R)-2-carboxy-3-phenyl-cyclopropyl)-methyl]-propylcarbamoyl}-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

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