(R)-[(E)-(3S,4R)-5-iodo-3,4-(isopropylidenedioxy)-1-pentenyl] p-tolyl sulfoxide

Base Information

Chemical Name:(R)-[(E)-(3S,4R)-5-iodo-3,4-(isopropylidenedioxy)-1-pentenyl] p-tolyl sulfoxide
CAS No.:311805-37-5
Molecular Formula:C₁₅H₁₉IO₃S
Molecular Weight:406.285
Hs Code.:

Synonyms:(R)-[(E)-(3S,4R)-5-iodo-3,4-(isopropylidenedioxy)-1-pentenyl] p-tolyl sulfoxide

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Chemical Property of (R)-[(E)-(3S,4R)-5-iodo-3,4-(isopropylidenedioxy)-1-pentenyl] p-tolyl sulfoxide

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Technology Process of (R)-[(E)-(3S,4R)-5-iodo-3,4-(isopropylidenedioxy)-1-pentenyl] p-tolyl sulfoxide

There total 5 articles about (R)-[(E)-(3S,4R)-5-iodo-3,4-(isopropylidenedioxy)-1-pentenyl] p-tolyl sulfoxide 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: 83.0%

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

: 311805-37-5
(R)-[(E)-(3S,4R)-5-iodo-3,4-(isopropylidenedioxy)-1-pentenyl] p-tolyl sulfoxide

Guidance literature:: With sodium hydrogencarbonate; sodium iodide; In acetone; for 5h; Heating;
DOI:10.1016/S0040-4020(00)00713-4

Reference yield:

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

: 311805-37-5
(R)-[(E)-(3S,4R)-5-iodo-3,4-(isopropylidenedioxy)-1-pentenyl] p-tolyl sulfoxide

Guidance literature:: Multi-step reaction with 4 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

4.1: 83 percent / NaI; NaHCO₃ / acetone / 5 h / Heating

With dmap; n-butyllithium; sodium hydrogencarbonate; triethylamine; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; acetone; 1.1: deprotonation / 1.2: Substitution / 2.1: Ring cleavage / 3.1: Tosylation / 4.1: Substitution;
DOI:10.1016/S0040-4020(00)00713-4

Reference yield:

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

: 311805-37-5
(R)-[(E)-(3S,4R)-5-iodo-3,4-(isopropylidenedioxy)-1-pentenyl] p-tolyl sulfoxide

Guidance literature:: Multi-step reaction with 4 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

4.1: 83 percent / NaI; NaHCO₃ / acetone / 5 h / Heating

With dmap; n-butyllithium; sodium hydrogencarbonate; triethylamine; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; acetone; 1.1: deprotonation / 1.2: Substitution / 2.1: Ring cleavage / 3.1: Tosylation / 4.1: Substitution;
DOI:10.1016/S0040-4020(00)00713-4