2H-Pyran, tetrahydro-2-methoxy-4-(methoxymethoxy)-6-[3-[(4-methoxyphenyl)meth oxy]propyl]-3,5-dimethyl-, (2R,3R,4S,5R,6S)-

Base Information

• Chemical Name: 2H-Pyran, tetrahydro-2-methoxy-4-(methoxymethoxy)-6-[3-[(4-methoxyphenyl)meth oxy]propyl]-3,5-dimethyl-, (2R,3R,4S,5R,6S)-
• CAS No.: 565229-08-5
• Molecular Formula: C21H34O6
• Molecular Weight: 382.497
• Mol file: 565229-08-5.mol

Synonyms:

Chemical Property of 2H-Pyran, tetrahydro-2-methoxy-4-(methoxymethoxy)-6-[3-[(4-methoxyphenyl)meth oxy]propyl]-3,5-dimethyl-, (2R,3R,4S,5R,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Pyran, tetrahydro-2-methoxy-4-(methoxymethoxy)-6-[3-[(4-methoxyphenyl)meth oxy]propyl]-3,5-dimethyl-, (2R,3R,4S,5R,6S)-

There total 12 articles about 2H-Pyran, tetrahydro-2-methoxy-4-(methoxymethoxy)-6-[3-[(4-methoxyphenyl)meth oxy]propyl]-3,5-dimethyl-, (2R,3R,4S,5R,6S)- 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: 64.0%

methanol (67-56-1) + 6-[(3R,4S,5S,6S)-3-(4-methoxybenzyloxy)propyl]-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-one (565229-05-2) → 2(R)-methoxy-6-[(3R,4S,5S,6S)-3-(4-methoxybenzyloxy)propyl]-4-methoxymethoxy-3,5-dimethyltetrahydropran (565229-08-5) + 2(S)-methoxy-6-[(3R,4S,5S,6S)-3-(4-methoxybenzyloxy)propyl]-4-methoxymethoxy-3,5-dimethyltetrahydropran

Guidance literature:

6-[(3R,4S,5S,6S)-3-(4-methoxybenzyloxy)propyl]-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-one; With diisobutylaluminium hydride; In tetrahydrofuran; dichloromethane; at -78 ℃; for 1h;

methanol; With pyridinium p-toluenesulfonate; at 20 ℃; for 15h;

Reference yield:

p-methoxybenzyl chloride (824-94-2) → 2(R)-methoxy-6-[(3R,4S,5S,6S)-3-(4-methoxybenzyloxy)propyl]-4-methoxymethoxy-3,5-dimethyltetrahydropran (565229-08-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 92 percent / NaH / dimethylformamide

2.1: pyridinium sulfur trioxide; N,N-diisopropylethylamine / CH₂Cl₂; dimethylsulfoxide / 1 h / 20 °C

3.1: Bu₂BOTf; N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

3.2: CH₂Cl₂ / 2.17 h / -78 - 0 °C

3.3: 87 percent / aq. H₂O₂; phosphate buffer / CH₂Cl₂; methanol / 1 h / 0 °C / pH 7.0

4.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 20 °C

5.1: 78 percent / lithium borohydride / tetrahydrofuran; methanol / 3.33 h / 0 - 20 °C

6.1: pyridinium sulfur trioxide; N,N-diisopropylethylamine / CH₂Cl₂; dimethylsulfoxide / 1 h / 20 °C

7.1: Bu₂BOTf; N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

7.2: CH₂Cl₂ / 2.17 h / -78 - 0 °C

7.3: 2.29 g / aq. H₂O₂; phosphate buffer / CH₂Cl₂; methanol / 1 h / pH 7.0

8.1: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / Heating

9.1: 83 percent / HF*pyridine; pyridine / methanol / 48 h / 20 °C

10.1: diisobutylaluminum hydride / tetrahydrofuran; CH₂Cl₂ / 1 h / -78 °C

11.1: pyridinium p-toluenesulfonate / 15 h / 20 °C

With pyridine; 2,6-dimethylpyridine; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1021/jm0204136

Reference yield:

4-(p-methoxybenzyloxy)butan-1-ol (119649-45-5) → 2(R)-methoxy-6-[(3R,4S,5S,6S)-3-(4-methoxybenzyloxy)propyl]-4-methoxymethoxy-3,5-dimethyltetrahydropran (565229-08-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: pyridinium sulfur trioxide; N,N-diisopropylethylamine / CH₂Cl₂; dimethylsulfoxide / 1 h / 20 °C

2.1: Bu₂BOTf; N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

2.2: CH₂Cl₂ / 2.17 h / -78 - 0 °C

2.3: 87 percent / aq. H₂O₂; phosphate buffer / CH₂Cl₂; methanol / 1 h / 0 °C / pH 7.0

3.1: 90 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 20 °C

4.1: 78 percent / lithium borohydride / tetrahydrofuran; methanol / 3.33 h / 0 - 20 °C

5.1: pyridinium sulfur trioxide; N,N-diisopropylethylamine / CH₂Cl₂; dimethylsulfoxide / 1 h / 20 °C

6.1: Bu₂BOTf; N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / 0 °C

6.2: CH₂Cl₂ / 2.17 h / -78 - 0 °C

6.3: 2.29 g / aq. H₂O₂; phosphate buffer / CH₂Cl₂; methanol / 1 h / pH 7.0

7.1: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / Heating

8.1: 83 percent / HF*pyridine; pyridine / methanol / 48 h / 20 °C

9.1: diisobutylaluminum hydride / tetrahydrofuran; CH₂Cl₂ / 1 h / -78 °C

10.1: pyridinium p-toluenesulfonate / 15 h / 20 °C

With pyridine; 2,6-dimethylpyridine; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jm0204136

upstream raw materials:

methanol

p-methoxybenzyl chloride

4-(p-methoxybenzyloxy)butan-1-ol

4-((4-methoxybenzyl)oxy)butanal

Downstream raw materials:

(2R,3S,4S,5Z)-3-(4-methoxybenzyloxy)-8-[(2S,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4-dimethyloct-5-enal

(4R,5S)-4-{(1S,2Z)-5-[(2S,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-1-methylpent-2-enyl}-2-(4-methoxyphenyl)-5-methyl[1,3]dioxane

(2S,3R,6Z,8S,9S,10S,11Z)-3,9-bis(4-methoxybenzyloxy)-14-[(2S,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,8,10-trimethyltetradeca-6,11-dienal

(4S,5R)-4-{(3Z,5S,6S,7S,8Z)-6-(4-methoxybenzyloxy)-11-[(2S,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-5,7-dimethylundeca-3,8-dienyl}-2-(4-methoxyphenyl)-5-methyl[1,3]dioxane