(2S,4S)-4-acetylthio-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonylpyrrolidine

Base Information

Chemical Name:(2S,4S)-4-acetylthio-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonylpyrrolidine
CAS No.:170587-06-1
Molecular Formula:C₂₁H₂₆N₂O₅S
Molecular Weight:418.514
Hs Code.:

Synonyms:(2S,4S)-4-acetylthio-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonylpyrrolidine

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Chemical Property of (2S,4S)-4-acetylthio-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonylpyrrolidine

Chemical Property:

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Technology Process of (2S,4S)-4-acetylthio-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonylpyrrolidine

There total 16 articles about (2S,4S)-4-acetylthio-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonylpyrrolidine 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:

: 87736-74-1
4-(tert-butyldimethylsiloxymethyl)bromobenzene

: 170587-06-1
(2S,4S)-4-acetylthio-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonylpyrrolidine

Guidance literature:: Multi-step reaction with 11 steps

1.1: 88.8 percent / n-BuLi / tetrahydrofuran; hexane / -70 °C

2.1: PPh₃; DEAD; DPPA / tetrahydrofuran / 0 °C

3.1: PPh₃ / tetrahydrofuran; H₂O / 5 h / 50 °C

3.2: Et₃N / tetrahydrofuran / 0 °C

4.1: MsCl; TEA / CH₂Cl₂ / 0 °C

4.2: NaN₃ / dimethylformamide / 20 °C

4.3: p-TsOH / methanol / 20 °C

5.1: 29.8 percent / imidazole / CH₂Cl₂ / 20 °C

6.1: PPh₃ / tetrahydrofuran; H₂O / 2 h / 20 °C

7.1: Et₃N / tetrahydrofuran / 0 °C

8.1: TBAF / tetrahydrofuran / 0 °C

9.1: Et₃N / CH₂Cl₂ / 0 °C

10.1: t-BuOK / tetrahydrofuran / -20 °C

11.1: dimethylformamide / 3 h / 65 °C

With 1H-imidazole; n-butyllithium; TEA; diphenyl-phosphinic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; methanesulfonyl chloride; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Condensation / 2.1: Substitution / 3.1: Reduction / 3.2: Acylation / 4.1: Substitution / 4.2: Substitution / 4.3: Hydrolysis / 5.1: silylation / 6.1: Reduction / 7.1: Acylation / 8.1: desilylation / 9.1: mesylation / 10.1: Cyclization / 11.1: Substitution;
DOI:10.1016/S0968-0896(00)00125-5

Reference yield:

: 304655-64-9
[(R)-1-(4-Azidomethyl-phenyl)-3,4-dihydroxy-butyl]-carbamic acid allyl ester

: 170587-06-1
(2S,4S)-4-acetylthio-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonylpyrrolidine

Guidance literature:: Multi-step reaction with 7 steps

1: 29.8 percent / imidazole / CH₂Cl₂ / 20 °C

2: PPh₃ / tetrahydrofuran; H₂O / 2 h / 20 °C

3: Et₃N / tetrahydrofuran / 0 °C

4: TBAF / tetrahydrofuran / 0 °C

5: Et₃N / CH₂Cl₂ / 0 °C

6: t-BuOK / tetrahydrofuran / -20 °C

7: dimethylformamide / 3 h / 65 °C

With 1H-imidazole; potassium tert-butylate; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1: silylation / 2: Reduction / 3: Acylation / 4: desilylation / 5: mesylation / 6: Cyclization / 7: Substitution;
DOI:10.1016/S0968-0896(00)00125-5

Reference yield:

: 228267-28-5
(3R)-1-(4-tert-butyldimethylsiloxymethylphenyl)-3,4-O-isopropylidene-3,4-dihydroxybutylazide

: 170587-06-1
(2S,4S)-4-acetylthio-2-[4-(N-allyloxycarbonylaminomethyl)phenyl]-1-allyloxycarbonylpyrrolidine

Guidance literature:: Multi-step reaction with 9 steps

1.1: PPh₃ / tetrahydrofuran; H₂O / 5 h / 50 °C

1.2: Et₃N / tetrahydrofuran / 0 °C

2.1: MsCl; TEA / CH₂Cl₂ / 0 °C

2.2: NaN₃ / dimethylformamide / 20 °C

2.3: p-TsOH / methanol / 20 °C

3.1: 29.8 percent / imidazole / CH₂Cl₂ / 20 °C

4.1: PPh₃ / tetrahydrofuran; H₂O / 2 h / 20 °C

5.1: Et₃N / tetrahydrofuran / 0 °C

6.1: TBAF / tetrahydrofuran / 0 °C

7.1: Et₃N / CH₂Cl₂ / 0 °C

8.1: t-BuOK / tetrahydrofuran / -20 °C

9.1: dimethylformamide / 3 h / 65 °C

With 1H-imidazole; TEA; potassium tert-butylate; tetrabutyl ammonium fluoride; methanesulfonyl chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Reduction / 1.2: Acylation / 2.1: Substitution / 2.2: Substitution / 2.3: Hydrolysis / 3.1: silylation / 4.1: Reduction / 5.1: Acylation / 6.1: desilylation / 7.1: mesylation / 8.1: Cyclization / 9.1: Substitution;
DOI:10.1016/S0968-0896(00)00125-5