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

Base Information

• Chemical Name: (2S,4R)-2-Allyloxycarbonylmethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 127767-92-4
• Molecular Formula: C₁₉H₂₄N₂O₁₀S
• Molecular Weight: 472.473

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

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

Chemical Property:

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

There total 10 articles about (2S,4R)-2-Allyloxycarbonylmethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl 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: 100.0%

allyl alcohol (107-18-6) + (2S,4R)-2-Carboxymethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester (117811-74-2) → (2S,4R)-2-Allyloxycarbonylmethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester (127767-92-4)

Guidance literature:

With sulfuric acid; for 5h; Heating;

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

Reference yield:

(2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (101803-29-6) → (2S,4R)-2-Allyloxycarbonylmethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester (127767-92-4)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; sulfuric acid; 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,4R)-2-Allyloxycarbonylmethoxymethyl-4-methanesulfonyloxy-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester (127767-92-4)

Guidance literature:

Multi-step reaction with 7 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

With hydrogenchloride; sodium hydroxide; sulfuric acid; hydrogen; sodium hydride; triethylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water;

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

upstream raw materials:

allyl alcohol

(2S,4R)-2-Carboxymethoxymethyl-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

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

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