1-acetoxy-3-(4-tetrahydropyranyloxy-3-methylphenyl)-2-(S)-tetrahydropyranyloxypropane

Base Information

• Chemical Name: 1-acetoxy-3-(4-tetrahydropyranyloxy-3-methylphenyl)-2-(S)-tetrahydropyranyloxypropane
• CAS No.: 443147-20-4
• Molecular Formula: C₂₂H₃₂O₆
• Molecular Weight: 392.492
• Mol file: 443147-20-4.mol

Synonyms:1-acetoxy-3-(4-tetrahydropyranyloxy-3-methylphenyl)-2-(S)-tetrahydropyranyloxypropane

Chemical Property of 1-acetoxy-3-(4-tetrahydropyranyloxy-3-methylphenyl)-2-(S)-tetrahydropyranyloxypropane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-acetoxy-3-(4-tetrahydropyranyloxy-3-methylphenyl)-2-(S)-tetrahydropyranyloxypropane

There total 4 articles about 1-acetoxy-3-(4-tetrahydropyranyloxy-3-methylphenyl)-2-(S)-tetrahydropyranyloxypropane 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:

3,4-dihydro-2H-pyran (110-87-2) + 2-(S)-1-acetoxy-3-(4-hydroxy-3-methylphenyl)propan-2-ol → 1-acetoxy-3-(4-tetrahydropyranyloxy-3-methylphenyl)-2-(S)-tetrahydropyranyloxypropane (443147-20-4)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃;

DOI:10.1016/S0968-0896(02)00031-7

Reference yield:

4-bromo-2-methyl-1-(2'-tetrahydropyranyloxy)benzene (148344-51-8) → 1-acetoxy-3-(4-tetrahydropyranyloxy-3-methylphenyl)-2-(S)-tetrahydropyranyloxypropane (443147-20-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Mg; CuI / tetrahydrofuran / 0 °C

1.2: 100 percent / tetrahydrofuran

2.1: AcOH; H₂O / tetrahydrofuran / 65 °C

3.1: 2,4,6-collidine / CH₂Cl₂ / -78 °C

4.1: p-TsOH*H₂O / CH₂Cl₂ / 20 °C

With 2,4,6-trimethyl-pyridine; copper(l) iodide; water; toluene-4-sulfonic acid; magnesium; acetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0968-0896(02)00031-7

Reference yield:

2-(S)-hydroxy-3-(4-hydroxy-3-methylphenyl)propan-1-ol → 1-acetoxy-3-(4-tetrahydropyranyloxy-3-methylphenyl)-2-(S)-tetrahydropyranyloxypropane (443147-20-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 2,4,6-collidine / CH₂Cl₂ / -78 °C

2: p-TsOH*H₂O / CH₂Cl₂ / 20 °C

With 2,4,6-trimethyl-pyridine; toluene-4-sulfonic acid; In dichloromethane;

DOI:10.1016/S0968-0896(02)00031-7

upstream raw materials:

3,4-dihydro-2H-pyran

4-bromo-2-methyl-1-(2'-tetrahydropyranyloxy)benzene

2-(S)-hydroxy-3-(4-tetrahydropyranyloxy-3-methylphenyl)propan-1-ol trityl ether

Downstream raw materials:

(Z)-7-((1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-but-1-enyl}-5-hydroxy-cyclopentyl)-hept-5-enoic acid methyl ester

4-[2-(3-(tert-butyl-dimethyl-silanyloxy)-2-{3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-but-1-enyl}-5-oxo-cyclopentyl)-ethylsulfanyl]-butyric acid methyl ester

4-[2-(3-(tert-butyl-dimethyl-silanyloxy)-2-{3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-but-1-enyl}-5-oxo-cyclopentyl)-2-hydroxy-ethylsulfanyl]-butyric acid methyl ester

(Z)-7-((1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-but-1-enyl}-5-oxo-cyclopentyl)-hept-5-enoic acid methyl ester