methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-(methoxycarbonyl)-4-(1-iodoethylidene)-3-pyrrolidineacetate

Base Information

• Chemical Name: methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-(methoxycarbonyl)-4-(1-iodoethylidene)-3-pyrrolidineacetate
• CAS No.: 1190409-82-5
• Molecular Formula: C₁₈H₂₂INO₆S
• Molecular Weight: 507.346

Synonyms:methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-(methoxycarbonyl)-4-(1-iodoethylidene)-3-pyrrolidineacetate

Chemical Property of methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-(methoxycarbonyl)-4-(1-iodoethylidene)-3-pyrrolidineacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-(methoxycarbonyl)-4-(1-iodoethylidene)-3-pyrrolidineacetate

There total 13 articles about methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-(methoxycarbonyl)-4-(1-iodoethylidene)-3-pyrrolidineacetate 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: 98.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-(methoxycarbonyl)-4-(1-iodoethylidene)-3-pyrrolidineacetic acid (1190409-97-2) → methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-(methoxycarbonyl)-4-(1-iodoethylidene)-3-pyrrolidineacetate (1190409-82-5)

Guidance literature:

In diethyl ether; at 20 ℃; Cooling with acetone-dry ice;

DOI:10.1021/ja9063475

Reference yield:

methyl (2S)-2-[[(4-methylphenyl)sulfonyl]-(2-butyn-1-yl)-amino]-4-(phenylseleno)butanoate (1190409-87-0) → methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-(methoxycarbonyl)-4-(1-iodoethylidene)-3-pyrrolidineacetate (1190409-82-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: dihydrogen peroxide / tetrahydrofuran; water / 16.5 h / 20 °C

2.1: (acetylacetonato)dicarbonylrhodium (l) / toluene / 13 h / 120 °C / 25858.1 Torr / Autoclave

3.1: methanol; sodium tetrahydroborate / 2 - 5 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 10 h / 20 °C / Inert atmosphere

5.1: Iodine monochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere

6.1: hydrogen fluoride; water / acetonitrile / 20 °C / Inert atmosphere

7.1: chromium(VI) oxide; periodic acid / water; acetonitrile / 0.43 h / -1 - 1 °C / Inert atmosphere

8.1: diethyl ether / 0.17 h / 20 °C

8.2: 0.17 h / 20 °C

With 1H-imidazole; chromium(VI) oxide; methanol; (acetylacetonato)dicarbonylrhodium (l); sodium tetrahydroborate; hydrogen fluoride; water; dihydrogen peroxide; Iodine monochloride; periodic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo101790z

Reference yield:

methyl (2S)-2-[[(4-methylphenyl)sulfonyl]amino]-4-(phenylseleno)butanoate (960004-39-1) → methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-(methoxycarbonyl)-4-(1-iodoethylidene)-3-pyrrolidineacetate (1190409-82-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: triphenylphosphine; diethylazodicarboxylate / dichloromethane / -1 - 1 °C / Inert atmosphere

2.1: dihydrogen peroxide / tetrahydrofuran; water / 16.5 h / 20 °C

3.1: (acetylacetonato)dicarbonylrhodium (l) / toluene / 13 h / 120 °C / 25858.1 Torr / Autoclave

4.1: methanol; sodium tetrahydroborate / 2 - 5 °C / Inert atmosphere

5.1: 1H-imidazole / N,N-dimethyl-formamide / 10 h / 20 °C / Inert atmosphere

6.1: Iodine monochloride / dichloromethane / 2 h / 20 °C / Inert atmosphere

7.1: hydrogen fluoride; water / acetonitrile / 20 °C / Inert atmosphere

8.1: chromium(VI) oxide; periodic acid / water; acetonitrile / 0.43 h / -1 - 1 °C / Inert atmosphere

9.1: diethyl ether / 0.17 h / 20 °C

9.2: 0.17 h / 20 °C

With 1H-imidazole; chromium(VI) oxide; methanol; (acetylacetonato)dicarbonylrhodium (l); sodium tetrahydroborate; hydrogen fluoride; water; dihydrogen peroxide; Iodine monochloride; periodic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Mitsunobu reaction;

DOI:10.1021/jo101790z

upstream raw materials:

diazomethane

(2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-(methoxycarbonyl)-4-(1-iodoethylidene)-3-pyrrolidineacetic acid

methyl (2S)-2-[[(4-methylphenyl)sulfonyl]amino]-4-(phenylseleno)butanoate

methyl (2S)-2-[[(4-methylphenyl)sulfonyl]-(2-butyn-1-yl)-amino]-4-(phenylseleno)butanoate

Downstream raw materials:

methyl (2S,3S,4E)-1-(4-methylphenylsulfonyl)-2-methoxycarbonyl-4-[(2E,5R)-5-methoxycarbonyl-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetate

(2S,3S,4E)-1-(4-methylphenylsulfonyl)-2-carboxy-4-[(2E,5R)-5-carboxy-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetic acid

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