methyl (2S,3S,4E)-1-[4-(methylphenyl)sulfonyl]-3-[2-(tris(1-methylethyl)silyloxy)ethyl]-4-[1-(dimethyl(phenyl)silyl)ethylidene]-2-pyrrolidinecarboxylate

Base Information

Chemical Name:methyl (2S,3S,4E)-1-[4-(methylphenyl)sulfonyl]-3-[2-(tris(1-methylethyl)silyloxy)ethyl]-4-[1-(dimethyl(phenyl)silyl)ethylidene]-2-pyrrolidinecarboxylate
CAS No.:1190409-92-7
Molecular Formula:C₃₄H₅₃NO₅SSi₂
Molecular Weight:644.036
Hs Code.:

methyl (2S,3S,4E)-1-[4-(methylphenyl)sulfonyl]-3-[2-(tris(1-methylethyl)silyloxy)ethyl]-4-[1-(dimethyl(phenyl)silyl)ethylidene]-2-pyrrolidinecarboxylate

Synonyms:methyl (2S,3S,4E)-1-[4-(methylphenyl)sulfonyl]-3-[2-(tris(1-methylethyl)silyloxy)ethyl]-4-[1-(dimethyl(phenyl)silyl)ethylidene]-2-pyrrolidinecarboxylate

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Chemical Property of methyl (2S,3S,4E)-1-[4-(methylphenyl)sulfonyl]-3-[2-(tris(1-methylethyl)silyloxy)ethyl]-4-[1-(dimethyl(phenyl)silyl)ethylidene]-2-pyrrolidinecarboxylate

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Technology Process of methyl (2S,3S,4E)-1-[4-(methylphenyl)sulfonyl]-3-[2-(tris(1-methylethyl)silyloxy)ethyl]-4-[1-(dimethyl(phenyl)silyl)ethylidene]-2-pyrrolidinecarboxylate

There total 9 articles about methyl (2S,3S,4E)-1-[4-(methylphenyl)sulfonyl]-3-[2-(tris(1-methylethyl)silyloxy)ethyl]-4-[1-(dimethyl(phenyl)silyl)ethylidene]-2-pyrrolidinecarboxylate 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: 91.0%

: 13154-24-0
triisopropylsilyl chloride

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

: 1190409-92-7
methyl (2S,3S,4E)-1-[4-(methylphenyl)sulfonyl]-3-[2-(tris(1-methylethyl)silyloxy)ethyl]-4-[1-(dimethyl(phenyl)silyl)ethylidene]-2-pyrrolidinecarboxylate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 10h; Inert atmosphere;
DOI:10.1021/ja9063475

Reference yield:

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

: 1190409-92-7
methyl (2S,3S,4E)-1-[4-(methylphenyl)sulfonyl]-3-[2-(tris(1-methylethyl)silyloxy)ethyl]-4-[1-(dimethyl(phenyl)silyl)ethylidene]-2-pyrrolidinecarboxylate

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

With 1H-imidazole; methanol; (acetylacetonato)dicarbonylrhodium (l); sodium tetrahydroborate; dihydrogen peroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; 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

: 1190409-92-7
methyl (2S,3S,4E)-1-[4-(methylphenyl)sulfonyl]-3-[2-(tris(1-methylethyl)silyloxy)ethyl]-4-[1-(dimethyl(phenyl)silyl)ethylidene]-2-pyrrolidinecarboxylate

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

With 1H-imidazole; methanol; (acetylacetonato)dicarbonylrhodium (l); sodium tetrahydroborate; dihydrogen peroxide; In tetrahydrofuran; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo101790z