tert-butyl (3S,4S,Z)-5-((dimethyl(phenyl)silyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate

Base Information

Chemical Name:tert-butyl (3S,4S,Z)-5-((dimethyl(phenyl)silyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate
CAS No.:1341205-66-0
Molecular Formula:C₁₉H₂₇NO₄Si
Molecular Weight:361.513
Hs Code.:

Synonyms:tert-butyl (3S,4S,Z)-5-((dimethyl(phenyl)silyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate

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Chemical Property of tert-butyl (3S,4S,Z)-5-((dimethyl(phenyl)silyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate

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Technology Process of tert-butyl (3S,4S,Z)-5-((dimethyl(phenyl)silyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate

There total 6 articles about tert-butyl (3S,4S,Z)-5-((dimethyl(phenyl)silyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate 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: 69.0%

: (2S,aS)-2-(tert-butoxycarbonylamino)-5-(dimethyl(phenyl)silyl)-3-methylpenta-3,4-dienoic acid

: tert-butyl (3S,4R,Z)-5-((dimethyl(phenyl)silyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate

: 1341205-66-0
tert-butyl (3S,4S,Z)-5-((dimethyl(phenyl)silyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate

Guidance literature:: With tris[triphenylphosphinegold(I)]oxonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/j.tetlet.2011.08.050

Reference yield:

: 791813-58-6
1-[dimethyl(phenyl)silyl]but-2-yn-1-ol

: tert-butyl (3S,4R,Z)-5-((dimethyl(phenyl)silyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate

: 1341205-66-0
tert-butyl (3S,4S,Z)-5-((dimethyl(phenyl)silyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-chloro-succinimide; N-(phenylthio)-N-(tert-butyl)amine; potassium carbonate

2.1: B-chlorodiisopinocampheylborane

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 0 - 20 °C

4.1: zinc(II) chloride; lithium diisopropyl amide / tetrahydrofuran; diethyl ether; hexane / 1.5 h / -78 - 20 °C

4.2: pH 1

5.1: tris[triphenylphosphinegold(I)]oxonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C

With dmap; N-chloro-succinimide; tris[triphenylphosphinegold(I)]oxonium tetrafluoroborate; N-(phenylthio)-N-(tert-butyl)amine; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; B-chlorodiisopinocampheylborane; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Mukaiyama oxidation;
DOI:10.1016/j.tetlet.2011.08.050

Reference yield:

: 791813-59-7
(S)-1-[dimethyl(phenyl)silyl]but-2-yn-1-ol

: tert-butyl (3S,4R,Z)-5-((dimethyl(phenyl)silyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate

: 1341205-66-0
tert-butyl (3S,4S,Z)-5-((dimethyl(phenyl)silyl)methylene)-4-methyl-2-oxotetrahydrofuran-3-ylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3 h / 0 - 20 °C

2.1: zinc(II) chloride; lithium diisopropyl amide / tetrahydrofuran; diethyl ether; hexane / 1.5 h / -78 - 20 °C

2.2: pH 1

3.1: tris[triphenylphosphinegold(I)]oxonium tetrafluoroborate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C

With dmap; tris[triphenylphosphinegold(I)]oxonium tetrafluoroborate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1016/j.tetlet.2011.08.050