(R)-2,2-Dimethyl-4-[(S)-1-((1S,2S,5R,6R)-4-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hex-2-yl)-propylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester

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Chemical Name:(R)-2,2-Dimethyl-4-[(S)-1-((1S,2S,5R,6R)-4-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hex-2-yl)-propylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester
CAS No.:331821-67-1
Molecular Formula:C₂₅H₃₄N₂O₅S
Molecular Weight:474.621
Hs Code.:

Synonyms:(R)-2,2-Dimethyl-4-[(S)-1-((1S,2S,5R,6R)-4-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hex-2-yl)-propylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester

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Chemical Property of (R)-2,2-Dimethyl-4-[(S)-1-((1S,2S,5R,6R)-4-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hex-2-yl)-propylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester

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Technology Process of (R)-2,2-Dimethyl-4-[(S)-1-((1S,2S,5R,6R)-4-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hex-2-yl)-propylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester

There total 15 articles about (R)-2,2-Dimethyl-4-[(S)-1-((1S,2S,5R,6R)-4-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hex-2-yl)-propylcarbamoyl]-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:

: 4440-01-1
lithium phenylacetylide

: 331821-67-1
(R)-2,2-Dimethyl-4-[(S)-1-((1S,2S,5R,6R)-4-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hex-2-yl)-propylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 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

With hydrogenchloride; triethylsilane; 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; diethyl ether; ethanol; 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

: 331821-67-1
(R)-2,2-Dimethyl-4-[(S)-1-((1S,2S,5R,6R)-4-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hex-2-yl)-propylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

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

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

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

4.1: 67 percent / 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

With hydrogenchloride; triethylsilane; 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; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 7.1: Mitsunobu cyclization;
DOI:10.1021/jo001257i

Reference yield:

: 241478-33-1
tert-butyl (4S)-4-<(1R)-1-hydroxy-3-phenyl-2-propynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

: 331821-67-1
(R)-2,2-Dimethyl-4-[(S)-1-((1S,2S,5R,6R)-4-oxo-6-phenyl-3-oxa-bicyclo[3.1.0]hex-2-yl)-propylcarbamoyl]-thiazolidine-3-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 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

With hydrogenchloride; triethylsilane; 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; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 7.1: Mitsunobu cyclization;
DOI:10.1021/jo001257i