(2S,4S)-4-acetylthio-2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Base Information

• Chemical Name: (2S,4S)-4-acetylthio-2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
• CAS No.: 127767-97-9
• Molecular Formula: C₂₀H₂₄N₂O₈S
• Molecular Weight: 452.485

Synonyms:(2S,4S)-4-acetylthio-2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Chemical Property of (2S,4S)-4-acetylthio-2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Chemical Property:

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Technology Process of (2S,4S)-4-acetylthio-2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

There total 12 articles about (2S,4S)-4-acetylthio-2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine 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: 74.0%

tiolacetic acid (507-09-5) + (2S,4R)-2-Allyloxycarbonylmethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester (127767-92-4) → (2S,4S)-4-acetylthio-2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (127767-97-9)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 75 - 80 ℃; for 3h;

DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

(2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (101803-29-6) → (2S,4S)-4-acetylthio-2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (127767-97-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / imidazole / dimethylformamide / 14 h / Ambient temperature

2: 48 percent / NaBH₄ / ethanol / 16 h / Ambient temperature

3: H₂ / 20percent Pd(OH)2/C / methanol / 3 h / 760 Torr / Ambient temperature

4: aq. NaOH / tetrahydrofuran / 2 h

5: 94 percent / NaH / tetrahydrofuran / 3 h / Ambient temperature

6: aq. 6N HCl / 3 h / Heating

7: 4N aq. NaOH / tetrahydrofuran; H₂O / 2 h

8: 75 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

9: 100 percent / H₂SO₄ / 5 h / Heating

10: 74 percent / t-BuOK / dimethylformamide / 3 h / 75 - 80 °C

With 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; sulfuric acid; potassium tert-butylate; hydrogen; sodium hydride; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(97)00142-9

Reference yield:

(2S,4R)-4-tert-butyldimethylsiloxy-2-hydroxymethyl-N-(4-nitrobenzyloxycarbonyl) pyrrolidine (104795-10-0) → (2S,4S)-4-acetylthio-2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (127767-97-9)

Guidance literature:

Multi-step reaction with 8 steps

1: H₂ / 20percent Pd(OH)2/C / methanol / 3 h / 760 Torr / Ambient temperature

2: aq. NaOH / tetrahydrofuran / 2 h

3: 94 percent / NaH / tetrahydrofuran / 3 h / Ambient temperature

4: aq. 6N HCl / 3 h / Heating

5: 4N aq. NaOH / tetrahydrofuran; H₂O / 2 h

6: 75 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

7: 100 percent / H₂SO₄ / 5 h / Heating

8: 74 percent / t-BuOK / dimethylformamide / 3 h / 75 - 80 °C

With hydrogenchloride; sodium hydroxide; sulfuric acid; potassium tert-butylate; hydrogen; sodium hydride; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(97)00142-9

upstream raw materials:

tiolacetic acid

(2S,4R)-2-Allyloxycarbonylmethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

(2S,4R)-4-t-butyldimethylsilyloxy-2-hydroxymethylpyrrolidine

(2S,4R)-2-carboxymethyloxymethyl-4-hydroxypyrrolidine

Downstream raw materials:

(4R,5S,6S)-3-[(3S,5S)-5-Allyloxycarbonylmethoxymethyl-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(2S,4S)-2-allyloxycarbonylmethyloxymethyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

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