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

Base Information

• Chemical Name: methyl (2S,3S,4Z)-1-(4-methylphenylsulfonyl)-2-methoxycarbonyl-4-[(2E,5R)-5-methoxycarbonyl-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetate
• CAS No.: 1190409-90-5
• Molecular Formula: C₂₅H₃₃NO₈S
• Molecular Weight: 507.605

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

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

There total 13 articles about methyl (2S,3S,4Z)-1-(4-methylphenylsulfonyl)-2-methoxycarbonyl-4-[(2E,5R)-5-methoxycarbonyl-1-methyl-2-hexen-1-ylidene]-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: 92.0%

methyl (R,E)-5-(hydroxydimethylsilyl)-2-methylpent-4-enoate (1190409-81-4) + methyl (2S,3S,4Z)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(iodo)ethylidene]-3-pyrrolidineacetate (1190409-83-6) → methyl (2S,3S,4Z)-1-(4-methylphenylsulfonyl)-2-methoxycarbonyl-4-[(2E,5R)-5-methoxycarbonyl-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetate (1190409-90-5)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrabutyl ammonium fluoride; In tetrahydrofuran; water; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jo101790z

Reference yield:

methyl (2S,3S,4Z)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(iodo)ethylidene]-3-pyrrolidineacetate (1190409-83-6) + (R,E)-methyl 5-(benzyldimethylsilyl)-2-methylpent-4-enoate (1259286-26-4) → methyl (2S,3S,4Z)-1-(4-methylphenylsulfonyl)-2-methoxycarbonyl-4-[(2E,5R)-5-methoxycarbonyl-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetate (1190409-90-5)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; naphthalene; tetrabutyl ammonium fluoride; In tetrahydrofuran; water; at 20 ℃; for 8h; Inert atmosphere;

DOI:10.1021/jo101790z

Reference yield:

C11H14INO4S → methyl (2S,3S,4Z)-1-(4-methylphenylsulfonyl)-2-methoxycarbonyl-4-[(2E,5R)-5-methoxycarbonyl-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetate (1190409-90-5)

Guidance literature:

Multi-step reaction with 10 steps

1: thionyl chloride / dichloromethane / 24 h / 20 °C / Inert atmosphere

2: sodium tetrahydroborate / ethanol / 8 - 21 °C / Inert atmosphere

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

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

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

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

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

8: diethyl ether; ethyl acetate / Inert atmosphere

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

10: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrabutyl ammonium fluoride / tetrahydrofuran; water / 1 h / 20 °C / Inert atmosphere

With chromium(VI) oxide; methanol; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (acetylacetonato)dicarbonylrhodium (l); sodium tetrahydroborate; thionyl chloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; Iodine monochloride; periodic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; toluene; acetonitrile; 3: Mitsunobu reaction;

DOI:10.1021/jo101790z

upstream raw materials:

methyl (R,E)-5-(hydroxydimethylsilyl)-2-methylpent-4-enoate

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

(2'R,4S)-4-benzyl-3-[2'-methylpent-4'-ynyloyl]oxazolidin-2-oneR

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

Downstream raw materials:

(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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