6β-hydroxywarburganal

Base Information

• Chemical Name: 6β-hydroxywarburganal
• CAS No.: 78424-45-0
• Molecular Formula: C₁₅H₂₂O₄
• Molecular Weight: 266.337
• Mol file: 78424-45-0.mol

Synonyms:

Chemical Property of 6β-hydroxywarburganal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6β-hydroxywarburganal

There total 10 articles about 6β-hydroxywarburganal 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: 92.0%

(5S,5aR,9aR,9bR)-1,3-Dimethoxy-6,6,9a-trimethyl-3,5,5a,6,7,8,9,9a-octahydro-naphtho[1,2-c]furan-5,9b-diol (78424-44-9) → 6β-hydroxywarburganal (78424-45-0,87420-14-2)

Guidance literature:

With hydrogenchloride; In acetone;

DOI:10.1021/ja00401a057

Reference yield:

(5aα,9aβ,9bα)-1,3,5,5a,6,7,8,9,9a,9b-decahydro-5-oxo-6,6,9a-trimethyl-9b-hydroxy-1,3-dimethoxynaphtho<1,2-c>furan (78424-43-8) → 6β-hydroxywarburganal (78424-45-0,87420-14-2)

Guidance literature:

With hydrogenchloride; diisobutylaluminium hydride; Yield given. Multistep reaction; 1.) THF, hexane, 1 h, 2.) acetone, 15 min;

DOI:10.1021/jo00203a014

Reference yield:

dimethyl 3,5,6,7,8,8a-hexahydro-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate (71557-96-5) → 6β-hydroxywarburganal (78424-45-0,87420-14-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) borane, 2.) H₂O₂, NaOH / 1.) THF

2: (i-Bu)2AlH / toluene / 1.) -78 deg C, 2.) 0 deg C, 2 h

3: pyridinium chlorochromate / CH₂Cl₂ / 1 h / Ambient temperature

4: 90 percent / benzene / 2 h / Ambient temperature

5: 70 percent / DBU / tetrahydrofuran / 0.33 h / Ambient temperature

6: 76 percent / m-chloroperbenzoic acid, Na₂CO₃ / CH₂Cl₂ / 1 h / Ambient temperature

7: 70 percent / p-toluenesulphonic acid / 10 h / Heating

8: 90 percent / (i-Bu)2AlH / tetrahydrofuran / 0.5 h / -5 °C

9: 92 percent / 10percent HCl / acetone

With hydrogenchloride; sodium hydroxide; borane; dihydrogen peroxide; diisobutylaluminium hydride; sodium carbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; acetone; toluene; benzene;

DOI:10.1021/ja00401a057

upstream raw materials:

(5S,5aR,9aR,9bR)-1,3-Dimethoxy-6,6,9a-trimethyl-3,5,5a,6,7,8,9,9a-octahydro-naphtho[1,2-c]furan-5,9b-diol

(5aα,9aβ,9bα)-1,3,5,5a,6,7,8,9,9a,9b-decahydro-5-oxo-6,6,9a-trimethyl-9b-hydroxy-1,3-dimethoxynaphtho<1,2-c>furan

dimethyl 3,5,6,7,8,8a-hexahydro-5,5,8a-trimethylnaphthalene-1,2-dicarboxylate

(1R,4aR,8aR)-3,4-Bis-hydroxymethyl-4a,8,8-trimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-ol

Downstream raw materials:

(+/-)-cinnamodial