(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

Base Information

• Chemical Name: (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
• CAS No.: 565229-32-5
• Molecular Formula: C₂₈H₄₄O₇
• Molecular Weight: 492.653
• Mol file: 565229-32-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 20 articles about (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 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:

(Z)-(2S,3S,4S)-3-(4-Methoxy-benzyloxy)-8-((2S,3R,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-2,4-dimethyl-oct-5-en-1-ol → (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 (565229-32-5)

Guidance literature:

With Dess-Martin periodane; In dichloromethane;

DOI:10.1021/jm0204136

Reference yield:

(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-2-methyl-hexanal (565229-01-8) → (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 (565229-32-5)

Guidance literature:

Multi-step reaction with 10 steps

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

1.2: CH₂Cl₂ / 2.17 h / -78 - 0 °C

1.3: 2.29 g / aq. H₂O₂; phosphate buffer / CH₂Cl₂; methanol / 1 h / pH 7.0

2.1: 92 percent / N,N-diisopropylethylamine / CH₂Cl₂ / Heating

3.1: 83 percent / HF*pyridine; pyridine / methanol / 48 h / 20 °C

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

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

6.1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C / atmospheric pressure

7.1: 274 mg / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

8.1: NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

8.2: 67 percent / tetrahydrofuran / 4.33 h / -78 - 20 °C

9.1: diisobutylaluminum hydride / hexane; CH₂Cl₂ / 2 h / 0 °C

10.1: 267 mg / Dess-Martin periodinane / CH₂Cl₂

With pyridine; di-n-butylboryl trifluoromethanesulfonate; hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; 7.1: Dess-Martin oxidation / 8.2: Wittig olefination / 10.1: Dess-Martin oxidation;

DOI:10.1021/jm0204136

Reference yield:

(3R,4S,5R,6S)-6-[3-(4-Methoxy-benzyloxy)-propyl]-4-methoxymethoxy-3,5-dimethyl-tetrahydro-pyran-2-ol → (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 (565229-32-5)

Guidance literature:

Multi-step reaction with 6 steps

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

2.1: H₂ / Pd/C / ethyl acetate / 3 h / 20 °C / atmospheric pressure

3.1: 274 mg / Dess-Martin periodinane / CH₂Cl₂ / 20 °C

4.1: NaHMDS / tetrahydrofuran / 0.33 h / 20 °C

4.2: 67 percent / tetrahydrofuran / 4.33 h / -78 - 20 °C

5.1: diisobutylaluminum hydride / hexane; CH₂Cl₂ / 2 h / 0 °C

6.1: 267 mg / Dess-Martin periodinane / CH₂Cl₂

With hydrogen; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 3.1: Dess-Martin oxidation / 4.2: Wittig olefination / 6.1: Dess-Martin oxidation;

DOI:10.1021/jm0204136

upstream raw materials:

p-Anisaldehyde dimethyl acetal

(2S)-2-[(4R,5S)-2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propan-1-ol

(R)-4-Benzyl-3-[(2R,3S,4S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2,4-dimethyl-pentanoyl]-oxazolidin-2-one

(2S)-tert-butyl-{(4R,5S)-2-[2-(4-methoxyphenyl)-5-methyl[1,3]dioxan-4-yl]propoxy}dimethylsilane

Downstream raw materials:

(1S,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-trimethyl-1-[(1S,2Z)-1-methylpenta-2,4-dienyl]tetradeca-6,11-dienyloxy]-tert-butyldimethylsilane

(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

(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

(1S,2S,3R,6Z,8S,9S,10S,11Z)-5,11-bis(4-methoxybenzyloxy)-16-[(2R,3S,4S,5R,6R)-6-methoxy-4-methoxymethoxy-3,5-dimethyltetrahydropyran-2-yl]-2,4,10,12-tetramethylhexadeca-8,13-dien-3-ol