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

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Chemical Name:(2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(phenyldimethylsilyl)ethylidene]-3-pyrrolidineacetic acid
CAS No.:1190409-96-1
Molecular Formula:C₂₅H₃₁NO₆SSi
Molecular Weight:501.676
Hs Code.:

Synonyms:(2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(phenyldimethylsilyl)ethylidene]-3-pyrrolidineacetic acid

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Chemical Property of (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(phenyldimethylsilyl)ethylidene]-3-pyrrolidineacetic acid

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Technology Process of (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(phenyldimethylsilyl)ethylidene]-3-pyrrolidineacetic acid

There total 9 articles about (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(phenyldimethylsilyl)ethylidene]-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: 84.0%

: 1190409-88-1
methyl (2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-3-(2-hydroxyethyl)-4-[1-(phenyldimethylsilyl)ethylidene]-2-pyrrolidinecarboxylate

: 1190409-96-1
(2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(phenyldimethylsilyl)ethylidene]-3-pyrrolidineacetic acid

Guidance literature:: With chromium(VI) oxide; periodic acid; In water; acetonitrile; at -1 - 1 ℃; for 0.583333h; Cooling with ice-salt bath;
DOI:10.1021/ja9063475

Reference yield:

: 960004-39-1
methyl (2S)-2-[[(4-methylphenyl)sulfonyl]amino]-4-(phenylseleno)butanoate

: 1190409-96-1
(2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(phenyldimethylsilyl)ethylidene]-3-pyrrolidineacetic acid

Guidance literature:: Multi-step reaction with 5 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

With chromium(VI) oxide; methanol; (acetylacetonato)dicarbonylrhodium (l); sodium tetrahydroborate; dihydrogen peroxide; periodic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; toluene; acetonitrile; 1: Mitsunobu reaction;
DOI:10.1021/jo101790z

Reference yield:

: 1190409-87-0
methyl (2S)-2-[[(4-methylphenyl)sulfonyl]-(2-butyn-1-yl)-amino]-4-(phenylseleno)butanoate

: 1190409-96-1
(2S,3S,4E)-1-[(4-methylphenyl)sulfonyl]-2-methoxycarbonyl-4-[1-(phenyldimethylsilyl)ethylidene]-3-pyrrolidineacetic acid

Guidance literature:: Multi-step reaction with 4 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

With chromium(VI) oxide; methanol; (acetylacetonato)dicarbonylrhodium (l); sodium tetrahydroborate; dihydrogen peroxide; periodic acid; In tetrahydrofuran; water; toluene; acetonitrile;
DOI:10.1021/jo101790z