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

Base Information

Chemical Name:(2S,3S,4Z)-1-(4-methylphenylsulfonyl)-2-carboxy-4-[(2E,5R)-5-carboxy-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetic acid
CAS No.:1190409-91-6
Molecular Formula:C₂₂H₂₇NO₈S
Molecular Weight:465.524
Hs Code.:

Synonyms:(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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Chemical Property of (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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Technology Process of (2S,3S,4Z)-1-(4-methylphenylsulfonyl)-2-carboxy-4-[(2E,5R)-5-carboxy-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetic acid

There total 15 articles about (2S,3S,4Z)-1-(4-methylphenylsulfonyl)-2-carboxy-4-[(2E,5R)-5-carboxy-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetic acid 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%

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

: 1190409-91-6
(2S,3S,4Z)-1-(4-methylphenylsulfonyl)-2-carboxy-4-[(2E,5R)-5-carboxy-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetic acid

Guidance literature:: With water; lithium hydroxide; In methanol; at 80 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ja9063475

Reference yield:

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

: 1190409-91-6
(2S,3S,4Z)-1-(4-methylphenylsulfonyl)-2-carboxy-4-[(2E,5R)-5-carboxy-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetic acid

Guidance literature:: Multi-step reaction with 2 steps

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

2: water; lithium hydroxide / methanol / 1 h / 80 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrabutyl ammonium fluoride; water; lithium hydroxide; In tetrahydrofuran; methanol; water;
DOI:10.1021/jo101790z

Reference yield:

: C₁₁H₁₄INO₄S

: 1190409-91-6
(2S,3S,4Z)-1-(4-methylphenylsulfonyl)-2-carboxy-4-[(2E,5R)-5-carboxy-1-methyl-2-hexen-1-ylidene]-3-pyrrolidineacetic acid

Guidance literature:: Multi-step reaction with 11 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

11: water; lithium hydroxide / methanol / 1 h / 80 °C / Inert atmosphere

With chromium(VI) oxide; methanol; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (acetylacetonato)dicarbonylrhodium (l); sodium tetrahydroborate; thionyl chloride; tetrabutyl ammonium fluoride; water; dihydrogen peroxide; Iodine monochloride; periodic acid; triphenylphosphine; lithium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; toluene; acetonitrile; 3: Mitsunobu reaction;
DOI:10.1021/jo101790z