methyl (2S,3S,4Z)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(iodo)ethylidene]-3-pyrrolidineacetate

Base Information

• Chemical Name: methyl (2S,3S,4Z)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(iodo)ethylidene]-3-pyrrolidineacetate
• CAS No.: 1190409-83-6
• Molecular Formula: C₁₈H₂₂INO₆S
• Molecular Weight: 507.346

Synonyms:methyl (2S,3S,4Z)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(iodo)ethylidene]-3-pyrrolidineacetate

Chemical Property of methyl (2S,3S,4Z)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(iodo)ethylidene]-3-pyrrolidineacetate

Chemical Property:

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Technology Process of methyl (2S,3S,4Z)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(iodo)ethylidene]-3-pyrrolidineacetate

There total 11 articles about methyl (2S,3S,4Z)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(iodo)ethylidene]-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: 86.0%

methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(phenyldimethylsilyl)ethylidene]-3-pyrrolidineacetate (1190409-89-2) → methyl (2S,3S,4Z)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(iodo)ethylidene]-3-pyrrolidineacetate (1190409-83-6)

Guidance literature:

With Iodine monochloride; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/ja9063475

Reference yield:

methyl (2S)-2-[[(4-methylphenyl)sulfonyl]amino]-4-(phenylseleno)butanoate (960004-39-1) → methyl (2S,3S,4Z)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(iodo)ethylidene]-3-pyrrolidineacetate (1190409-83-6)

Guidance literature:

Multi-step reaction with 7 steps

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

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

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

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

5: chromium(VI) oxide; periodic acid / water; acetonitrile / -1 - 6 °C

6: diethyl ether; ethyl acetate / Inert atmosphere

7: Iodine monochloride / dichloromethane / 1 h / 20 °C / Inert atmosphere

With chromium(VI) oxide; methanol; (acetylacetonato)dicarbonylrhodium (l); sodium tetrahydroborate; dihydrogen peroxide; Iodine monochloride; periodic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; toluene; acetonitrile; 1: Mitsunobu reaction;

DOI:10.1021/jo101790z

Reference yield:

methyl (2S)-2-[[(4-methylphenyl)sulfonyl]-(2-butyn-1-yl)-amino]-4-(phenylseleno)butanoate (1190409-87-0) → methyl (2S,3S,4Z)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(iodo)ethylidene]-3-pyrrolidineacetate (1190409-83-6)

Guidance literature:

Multi-step reaction with 6 steps

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

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

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

4: chromium(VI) oxide; periodic acid / water; acetonitrile / -1 - 6 °C

5: diethyl ether; ethyl acetate / Inert atmosphere

6: Iodine monochloride / dichloromethane / 1 h / 20 °C / Inert atmosphere

With chromium(VI) oxide; methanol; (acetylacetonato)dicarbonylrhodium (l); sodium tetrahydroborate; dihydrogen peroxide; Iodine monochloride; periodic acid; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; toluene; acetonitrile;

DOI:10.1021/jo101790z

upstream raw materials:

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

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

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

(2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(phenyldimethylsilyl)ethylidene]-3-pyrrolidineacetaldehyde

Downstream raw materials:

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

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

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