(S)-3-[(E)-(R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-pent-4-enyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

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Chemical Name:(S)-3-[(E)-(R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-pent-4-enyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one
CAS No.:507480-53-7
Molecular Formula:C₂₂H₃₃IO₃SSi
Molecular Weight:532.558
Hs Code.:

Synonyms:(S)-3-[(E)-(R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-pent-4-enyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

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Chemical Property of (S)-3-[(E)-(R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-pent-4-enyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

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Technology Process of (S)-3-[(E)-(R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-pent-4-enyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

There total 5 articles about (S)-3-[(E)-(R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-pent-4-enyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one 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: 54.0%

: 184435-75-4
(5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one

: 507480-52-6
(E,R)-1-(trifluoromethanesulfonyloxy)-2-(tert-butyldimethylsilyloxy)-5-iodo-4-pentene

: 507480-53-7
(S)-3-[(E)-(R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-pent-4-enyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

Guidance literature:: (5S)-5-methyl-3-phenylsulfanyl-4,5-dihydrofuran-2(3H)-one; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.333333h;

(E,R)-1-(trifluoromethanesulfonyloxy)-2-(tert-butyldimethylsilyloxy)-5-iodo-4-pentene; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; for 19h; Further stages.;
DOI:10.1021/jo026433x

Reference yield:

: 103-04-8
(phenylthio)acetic acid

: 507480-53-7
(S)-3-[(E)-(R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-pent-4-enyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: LDA

1.2: 86 percent / PTSA / benzene

2.1: i-Pr₂NH; BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

2.2: 54 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 19 h

With n-butyllithium; diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane;
DOI:10.1021/jo026433x

Reference yield:

: 507480-50-4
(E,R)-5-iodo-4-pentene-1,2-diol

: 507480-53-7
(S)-3-[(E)-(R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-pent-4-enyl]-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 0.85 g / 2,6-lutidine / CH₂Cl₂ / 1.5 h / cooling

3.1: i-Pr₂NH; BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.2: 54 percent / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 19 h

With 2,6-dimethylpyridine; n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo026433x