(E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-penten-1-ol

Base Information

Chemical Name:(E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-penten-1-ol
CAS No.:311805-35-3
Molecular Formula:C₁₅H₂₀O₄S
Molecular Weight:296.387
Hs Code.:

Synonyms:(E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-penten-1-ol

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Chemical Property of (E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-penten-1-ol

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Technology Process of (E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-penten-1-ol

There total 3 articles about (E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-penten-1-ol 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: 92.0%

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

: 311805-35-3
(E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-penten-1-ol

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;
DOI:10.1016/S0040-4020(00)00713-4

Reference yield:

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

: 311805-35-3
(E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-penten-1-ol

Guidance literature:: Multi-step reaction with 2 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

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

Reference yield:

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

: 311805-35-3
(E)-(2R,3S)-2,3-(isopropylidenedioxy)-5-[(R)-(p-tolylsulfinyl)]-4-penten-1-ol

Guidance literature:: Multi-step reaction with 2 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

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