(4S,5S)-4-(iodomethyl)-2,2-dimethyl-5-[(E)-2-[(p-tolyl)sulfonyl]-2-(methylthio)ethenyl]-1,3-dioxalane

Base Information

• Chemical Name: (4S,5S)-4-(iodomethyl)-2,2-dimethyl-5-[(E)-2-[(p-tolyl)sulfonyl]-2-(methylthio)ethenyl]-1,3-dioxalane
• CAS No.: 361203-44-3
• Molecular Formula: C₁₆H₂₁IO₄S₂
• Molecular Weight: 468.377
• Mol file: 361203-44-3.mol

Synonyms:(4S,5S)-4-(iodomethyl)-2,2-dimethyl-5-[(E)-2-[(p-tolyl)sulfonyl]-2-(methylthio)ethenyl]-1,3-dioxalane

Chemical Property of (4S,5S)-4-(iodomethyl)-2,2-dimethyl-5-[(E)-2-[(p-tolyl)sulfonyl]-2-(methylthio)ethenyl]-1,3-dioxalane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-4-(iodomethyl)-2,2-dimethyl-5-[(E)-2-[(p-tolyl)sulfonyl]-2-(methylthio)ethenyl]-1,3-dioxalane

There total 4 articles about (4S,5S)-4-(iodomethyl)-2,2-dimethyl-5-[(E)-2-[(p-tolyl)sulfonyl]-2-(methylthio)ethenyl]-1,3-dioxalane 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: 80.0%

{(4R,5S)-2,2-dimethyl-5-[(E)-2-[(p-tolyl)sulfonyl]-2-(methylthio)ethenyl]-1,3-dioxolan-4-yl}methyl methanesulfonate (361203-41-0) → (3aS,7aS)-2,2-dimethyl-6-[(p-tolyl)sulfonyl]-3a,7a-dihydro-4H-thiopyrano[3,4-d][1,3]dioxole (361203-48-7) + (4S,5S)-4-(iodomethyl)-2,2-dimethyl-5-[(E)-2-[(p-tolyl)sulfonyl]-2-(methylthio)ethenyl]-1,3-dioxalane (361203-44-3)

Guidance literature:

With sodium iodide; In acetonitrile; for 4h; Heating;

DOI:10.1002/jhet.5570380304

Reference yield:

2,3-O-isopropylidene-D-erythrose (189996-60-9) → (4S,5S)-4-(iodomethyl)-2,2-dimethyl-5-[(E)-2-[(p-tolyl)sulfonyl]-2-(methylthio)ethenyl]-1,3-dioxalane (361203-44-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: nBuLi; 12-crown-4 / tetrahydrofuran; hexane / -78 - 0 °C

1.2: 61 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

2.1: 80 percent / pyridine / 12 h / 0 - 20 °C

3.1: 80 percent / NaI / acetonitrile / 4 h / Heating

With pyridine; n-butyllithium; (1,4,7,10-tetraoxacyclododecane); sodium iodide; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1002/jhet.5570380304

Reference yield:

methylthiomethyl p-tolyl sulfone (59662-65-6) → (4S,5S)-4-(iodomethyl)-2,2-dimethyl-5-[(E)-2-[(p-tolyl)sulfonyl]-2-(methylthio)ethenyl]-1,3-dioxalane (361203-44-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: nBuLi; 12-crown-4 / tetrahydrofuran; hexane / -78 - 0 °C

1.2: 61 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

2.1: 80 percent / pyridine / 12 h / 0 - 20 °C

3.1: 80 percent / NaI / acetonitrile / 4 h / Heating

With pyridine; n-butyllithium; (1,4,7,10-tetraoxacyclododecane); sodium iodide; In tetrahydrofuran; hexane; acetonitrile;

DOI:10.1002/jhet.5570380304

upstream raw materials:

{(4R,5S)-2,2-dimethyl-5-[(E)-2-[(p-tolyl)sulfonyl]-2-(methylthio)ethenyl]-1,3-dioxolan-4-yl}methyl methanesulfonate

2,3-O-isopropylidene-D-erythrose

methylthiomethyl p-tolyl sulfone

1-[(4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(p-tolyl)sulfonyl]-2-(mthylthio)-1-ethanol

Downstream raw materials:

(3aS,7aS)-2,2-dimethyl-6-[(p-tolyl)sulfonyl]-3a,7a-dihydro-4H-thiopyrano[3,4-d][1,3]dioxole