(R)-4-((S)-1-{(S)-(tert-Butyl-dimethyl-silanyloxy)-[(1S,2R,3S)-2-((S)-1-methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-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,3S)-2-((S)-1-methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-phenyl-cyclopropyl]-methyl}-propylcarbamoyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester
CAS No.:331821-46-6
Molecular Formula:C₃₇H₆₁N₃O₇S₂Si
Molecular Weight:752.125
Hs Code.:

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

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

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

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

There total 16 articles about (R)-4-((S)-1-{(S)-(tert-Butyl-dimethyl-silanyloxy)-[(1S,2R,3S)-2-((S)-1-methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-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:

: 154437-23-7
trans-[4S,4(1'S)]-4-(1'-hydroxy-3'-phenyl-2'-propenyl)-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester

: 331821-46-6
(R)-4-((S)-1-{(S)-(tert-Butyl-dimethyl-silanyloxy)-[(1S,2R,3S)-2-((S)-1-methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-phenyl-cyclopropyl]-methyl}-propylcarbamoyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

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

2.1: Et₃N / CH₂Cl₂ / 0.42 h / 0 - 20 °C

3.1: 71 percent / Cu(TBS)2 / toluene / Heating

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

5.1: 2.61 g / Et₃N / acetonitrile / 12 h / 20 °C

6.1: 91 percent / DEAD; PPh₃ / tetrahydrofuran / 3.5 h / 20 °C

7.1: CuBr*DMS / diethyl ether / 0 °C

7.2: 93 percent / diethyl ether; CH₂Cl₂ / 0.17 h / 0 - 20 °C

8.1: HCl / dioxane / 0.5 h / Heating

9.1: 240 mg / Et₃N; HOBt; DCC / CH₂Cl₂; dimethylformamide / 3 h / 0 °C

10.1: aq. NaOH / ethanol / 1 h

11.1: methanol; diethyl ether

12.1: 123 mg / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 - -20 °C

13.1: 64 percent / NaOH / ethanol / 1 h / 20 °C

14.1: 71 percent / HOBt; Et₃N; DCC / CH₂Cl₂; dimethylformamide / 72 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; triethylsilane; sodium hydroxide; copper(I) bromide dimethylsulfide complex; benzotriazol-1-ol; N,N-dimethyl-aniline; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; Cu(TBS)2; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 6.1: Mitsunobu cyclization;
DOI:10.1021/jo001257i

Reference yield:

: 536-74-3
phenylacetylene

: 331821-46-6
(R)-4-((S)-1-{(S)-(tert-Butyl-dimethyl-silanyloxy)-[(1S,2R,3S)-2-((S)-1-methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-phenyl-cyclopropyl]-methyl}-propylcarbamoyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 16 steps

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

1.2: 8 percent / tetrahydrofuran; hexane / 2.25 h / -78 °C

2.1: 78 percent / Red-Al / diethyl ether / 0.92 h / 0 - 20 °C

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

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

5.1: 71 percent / Cu(TBS)2 / toluene / Heating

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

7.1: 2.61 g / Et₃N / acetonitrile / 12 h / 20 °C

8.1: 91 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: 240 mg / Et₃N; HOBt; DCC / CH₂Cl₂; dimethylformamide / 3 h / 0 °C

12.1: aq. NaOH / ethanol / 1 h

13.1: methanol; diethyl ether

14.1: 123 mg / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 - -20 °C

15.1: 64 percent / NaOH / ethanol / 1 h / 20 °C

16.1: 71 percent / HOBt; Et₃N; DCC / CH₂Cl₂; dimethylformamide / 72 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; triethylsilane; sodium hydroxide; n-butyllithium; copper(I) bromide dimethylsulfide complex; 18-crown-6 ether; benzotriazol-1-ol; N,N-dimethyl-aniline; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; 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:

: 241478-34-2
tert-butyl (4S)-4-<(1S)-1-hydroxy-3-phenyl-2-propynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 331821-46-6
(R)-4-((S)-1-{(S)-(tert-Butyl-dimethyl-silanyloxy)-[(1S,2R,3S)-2-((S)-1-methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-3-phenyl-cyclopropyl]-methyl}-propylcarbamoyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 15 steps

1.1: 78 percent / Red-Al / diethyl ether / 0.92 h / 0 - 20 °C

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

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

4.1: 71 percent / Cu(TBS)2 / toluene / Heating

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

6.1: 2.61 g / Et₃N / acetonitrile / 12 h / 20 °C

7.1: 91 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: 240 mg / Et₃N; HOBt; DCC / CH₂Cl₂; dimethylformamide / 3 h / 0 °C

11.1: aq. NaOH / ethanol / 1 h

12.1: methanol; diethyl ether

13.1: 123 mg / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 - -20 °C

14.1: 64 percent / NaOH / ethanol / 1 h / 20 °C

15.1: 71 percent / HOBt; Et₃N; DCC / CH₂Cl₂; dimethylformamide / 72 h / 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; triethylsilane; sodium hydroxide; copper(I) bromide dimethylsulfide complex; benzotriazol-1-ol; N,N-dimethyl-aniline; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; sodium bis(2-methoxyethoxy)aluminium dihydride; 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