4-Methoxy-6-((1R,2R,4aS,8aR)-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-2-oxo-2H-pyran-3-carbaldehyde

Base Information

• Chemical Name: 4-Methoxy-6-((1R,2R,4aS,8aR)-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-2-oxo-2H-pyran-3-carbaldehyde
• CAS No.: 112573-32-7
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.37
• Mol file: 112573-32-7.mol

Synonyms:

Chemical Property of 4-Methoxy-6-((1R,2R,4aS,8aR)-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-2-oxo-2H-pyran-3-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Methoxy-6-((1R,2R,4aS,8aR)-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-2-oxo-2H-pyran-3-carbaldehyde

There total 43 articles about 4-Methoxy-6-((1R,2R,4aS,8aR)-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-2-oxo-2H-pyran-3-carbaldehyde 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: 86.0%

Hydroxy-[4-methoxy-6-((1R,2S,4aR,8aR)-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-2-oxo-2H-pyran-3-yl]-acetic acid → (+/-)-solanopyrane A (88899-61-0,106973-16-4,112571-99-0,112573-32-7,112791-36-3,112791-37-4)

Guidance literature:

With sodium periodate; silica gel; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(03)00288-0

Reference yield:

(+/-)-solanapyrone B → (+)-solanapyrone B (88899-60-9) + (-)-solanapyrone B (88899-60-9) + solanopyrone A (88899-61-0,106973-16-4,112571-99-0,112573-32-7,112791-36-3,112791-37-4) + (-)-solanapyrone A (88899-61-0)

Guidance literature:

With potassium phosphate buffer; enzyme from A_. solani; In ethanol; at 30 ℃; for 2h; Yield given; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo980743r

Reference yield:

(2-[(N-benzylprolyl)amino]benzophenone) (95019-19-5) → (+/-)-solanopyrane A (88899-61-0,106973-16-4,112571-99-0,112573-32-7,112791-36-3,112791-37-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 83 percent / toluene

2.1: 69 percent / toluene / 144 h / 165 °C

3.1: NaH / tetrahydrofuran

3.2: 81 percent / n-BuLi / 0 °C

4.1: CF₃COOH / CH₂Cl₂

4.2: Ac₂O

4.3: 63 percent / NaHCO₃ / 20 °C

5.1: 83 percent / Et₃N / CH₂Cl₂ / 20 °C

6.1: NaBH₄ / methanol / 20 °C

6.2: 70 percent / NaOH / H₂O / 20 °C

7.1: 86 percent / NaIO₄; SiO₂ / CH₂Cl₂ / 20 °C

With sodium tetrahydroborate; sodium periodate; silica gel; sodium hydride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Wittig reaction / 2.1: Diels-Alder reaction;

DOI:10.1016/S0040-4039(03)00288-0

upstream raw materials:

(+)-solanapyrone B

prosolanapyrone III

3-[1,3]Dithian-2-yl-4-methoxy-6-((1S,2S,4aR,8aS)-2-methyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl)-pyran-2-one

(2-[(N-benzylprolyl)amino]benzophenone)