(E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-pentenyl p-toluenesulfonate

Base Information

Chemical Name:(E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-pentenyl p-toluenesulfonate
CAS No.:311805-36-4
Molecular Formula:C₂₂H₂₆O₆S₂
Molecular Weight:450.577
Hs Code.:

Synonyms:(E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-pentenyl p-toluenesulfonate

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Chemical Property of (E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-pentenyl p-toluenesulfonate

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Technology Process of (E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-pentenyl p-toluenesulfonate

There total 3 articles about (E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-pentenyl p-toluenesulfonate 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:

: 189996-60-9
2,3-O-isopropylidene-D-erythrose

: 311805-36-4
(E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-pentenyl p-toluenesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 96 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: 92 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

3.1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 3.5 h / 20 °C

With dmap; n-butyllithium; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 1.1: deprotonation / 1.2: Substitution / 2.1: Ring cleavage / 3.1: Tosylation;
DOI:10.1016/S0040-4020(00)00713-4

Reference yield:

: 61187-71-1
(+)-(R)-(dimethoxyphosphoryl)methyl p-tolyl sulfoxide

: 311805-36-4
(E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-pentenyl p-toluenesulfonate

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 96 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: 92 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

3.1: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 3.5 h / 20 °C

With dmap; n-butyllithium; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 1.1: deprotonation / 1.2: Substitution / 2.1: Ring cleavage / 3.1: Tosylation;
DOI:10.1016/S0040-4020(00)00713-4

Reference yield:

: 311805-34-2
(R)-[(3S,4R)-3,4-(isopropylidenedioxy)-2,5-epoxy-1-pentenyl] p-tolyl sulfoxide

: 311805-36-4
(E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-pentenyl p-toluenesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

2: 93 percent / Et₃N; DMAP / CH₂Cl₂ / 3.5 h / 20 °C

With dmap; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 1: Ring cleavage / 2: Tosylation;
DOI:10.1016/S0040-4020(00)00713-4