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

Base Information

• Chemical Name: (2S,4S)-2-allyloxycarbonylmethyloxymethyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine
• CAS No.: 127768-03-0
• Molecular Formula: C₁₈H₂₂N₂O₇S
• Molecular Weight: 410.448

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

There total 11 articles about (2S,4S)-2-allyloxycarbonylmethyloxymethyl-4-mercapto-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:

(2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (101803-29-6) → (2S,4S)-2-allyloxycarbonylmethyloxymethyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (127768-03-0)

Guidance literature:

Multi-step reaction with 11 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

11: NaH / various solvent(s) / 1 h

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)-2-allyloxycarbonylmethyloxymethyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (127768-03-0)

Guidance literature:

Multi-step reaction with 9 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

9: NaH / various solvent(s) / 1 h

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

Reference yield:

(2S,4R)-4-t-butyldimethylsilyloxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (117811-69-5) → (2S,4S)-2-allyloxycarbonylmethyloxymethyl-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (127768-03-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 48 percent / NaBH₄ / ethanol / 16 h / Ambient temperature

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

3: aq. NaOH / tetrahydrofuran / 2 h

4: 94 percent / NaH / tetrahydrofuran / 3 h / Ambient temperature

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

6: 4N aq. NaOH / tetrahydrofuran; H₂O / 2 h

7: 75 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 5 °C

8: 100 percent / H₂SO₄ / 5 h / Heating

9: 74 percent / t-BuOK / dimethylformamide / 3 h / 75 - 80 °C

10: NaH / various solvent(s) / 1 h

With 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

upstream raw materials:

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

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

(6S,8R)-8-t-butyldimethylsilyloxy-2-oxo-1-aza-4-oxabicyclo[4.3.0]nonane

(2S,4R)-4-t-butyldimethylsilyloxy-1-chloroacetyl-2-(hydroxymethyl)pyrrolidine

Downstream raw materials:

allyl (4R,5S,6S)-3-[(2S,4S)-2-(allyloxycarbonylmethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1azabicyclo[3.2.0]hept-2-ene-2-carboxylate

(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

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