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

Base Information

• Chemical Name: 1-[(4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(p-tolyl)sulfonyl]-2-(methylthio)-1-ethanol
• CAS No.: 361203-38-5
• Molecular Formula: C₁₆H₂₄O₆S₂
• Molecular Weight: 376.495
• Mol file: 361203-38-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 1-[(4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(p-tolyl)sulfonyl]-2-(methylthio)-1-ethanol 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: 61.0%

2,3-O-isopropylidene-L-erythrofuranose (213767-09-0) + methylthiomethyl p-tolyl sulfone (59662-65-6) → 1-[(4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(p-tolyl)sulfonyl]-2-(methylthio)-1-ethanol (361203-38-5)

Guidance literature:

methylthiomethyl p-tolyl sulfone; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃;

2,3-O-isopropylidene-L-erythrofuranose; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 12h;

DOI:10.1002/jhet.5570380304

Reference yield: 80.0%

methanesulfonyl chloride (124-63-0) + 1-[(4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(p-tolyl)sulfonyl]-2-(methylthio)-1-ethanol (361203-38-5) → {(4S,5R)-2,2-dimethyl-5-[(E)-2-[(p-tolyl)sulfonyl]-2-(methylthio)ethenyl]-1,3-dioxolan-4-yl}methyl methanesulfonate (361203-42-1)

Guidance literature:

With pyridine; at 0 - 20 ℃; for 12h;

DOI:10.1002/jhet.5570380304

Reference yield:

1-[(4R,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(p-tolyl)sulfonyl]-2-(methylthio)-1-ethanol (361203-38-5) → (3aR,6S,7aR)-2,2-dimethyl-6-[(p-tolyl)sulfonyl]tetrahydro-4H-thiopyrano[3,4-d][1,3]dioxole

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / pyridine / 12 h / 0 - 20 °C

2: 66 percent / NaI / dimethylformamide / 4 h / Heating

3: 44 percent / H₂ / 10 percent Pd/C / ethyl acetate / 5 h / 20 °C

With pyridine; hydrogen; sodium iodide; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1002/jhet.5570380304

upstream raw materials:

2,3-O-isopropylidene-L-erythrofuranose

methylthiomethyl p-tolyl sulfone

Downstream raw materials:

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

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

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