Bicyclo[3.2.0]hept-6-en-2-ol, 5-methoxy-1-methyl-, (1R,2R,5S)-rel-

Base Information

• Chemical Name: Bicyclo[3.2.0]hept-6-en-2-ol, 5-methoxy-1-methyl-, (1R,2R,5S)-rel-
• CAS No.: 109306-60-7
• Molecular Formula: C₉H₁₄O₂
• Molecular Weight: 154.209
• Mol file: 109306-60-7.mol

Synonyms:

Chemical Property of Bicyclo[3.2.0]hept-6-en-2-ol, 5-methoxy-1-methyl-, (1R,2R,5S)-rel-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bicyclo[3.2.0]hept-6-en-2-ol, 5-methoxy-1-methyl-, (1R,2R,5S)-rel-

There total 1 articles about Bicyclo[3.2.0]hept-6-en-2-ol, 5-methoxy-1-methyl-, (1R,2R,5S)-rel- 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:

trans-1,2-dichloroethylene (156-60-5,43695-79-0) + 3-methoxy-2-methylcyclopent-2-enone (3883-56-5) → 1-methyl-5-methoxybicyclo<3.2.0>hept-6-en-endo-2-ol (109306-60-7)

Guidance literature:

Yield given. Multistep reaction;

DOI:10.1021/jo00392a019

Reference yield:

1-methyl-5-methoxybicyclo<3.2.0>hept-6-en-endo-2-ol (109306-60-7) → Toluene-4-sulfonic acid (1S,3aR,3bR,6aS,6bS)-3a-methoxy-6b-methyl-4-oxo-decahydro-cyclobutadicyclopenten-1-yl ester

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Co₂(CO)8, / 1.) DME, 1h, 25 deg.C 2.) DME, 4d, 60-65 deg.C

2: 98 percent / H₂ / 5percent Pd/C / methanol / 60 h

3: 1.) KH / 1.) DMSO, 60 deg.C, 10 min, 2.) DMSO, 60 deg.C, 6h

4: 79 percent / pyridine / 48 h / Ambient temperature

With pyridine; dicobalt octacarbonyl; hydrogen; potassium hydride; palladium on activated charcoal; In methanol;

DOI:10.1021/jo00392a019

Reference yield:

1-methyl-5-methoxybicyclo<3.2.0>hept-6-en-endo-2-ol (109306-60-7) → cis-2-methyl-endo-8-<<(tert-butyldiphenylsilyl)oxy>methyl>bicyclo<5.3.0>dec-2-en-6-one (109306-80-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Co₂(CO)8, / 1.) DME, 1h, 25 deg.C 2.) DME, 4d, 60-65 deg.C

2: 98 percent / H₂ / 5percent Pd/C / methanol / 60 h

3: 1.) KH / 1.) DMSO, 60 deg.C, 10 min, 2.) DMSO, 60 deg.C, 6h

4: 1.)BH₃*SMe₂, 2.)NaOH, ethanol, 30percent H₂O₂ / 1.) THF, RT, 4h, 2.) THF, 60 deg. C, 1h

5: 76 percent / (C₂H₅)3N, DMAP / CH₂Cl₂ / 12 h

6: 96 percent / pyridine / 48 h / Ambient temperature

7: 72 percent / 15percent CH₃OH aq., CaCO₃, NaHCO₃ / pyridine / 72 h / Heating

With methanol; dmap; sodium hydroxide; dicobalt octacarbonyl; ethanol; dimethylsulfide borane complex; hydrogen; dihydrogen peroxide; potassium hydride; sodium hydrogencarbonate; triethylamine; calcium carbonate; palladium on activated charcoal; In pyridine; methanol; dichloromethane;

DOI:10.1021/jo00392a019

upstream raw materials:

trans-1,2-dichloroethylene

3-methoxy-2-methylcyclopent-2-enone

Downstream raw materials:

cis-2-methyl-endo-8-<<(tert-butyldiphenylsilyl)oxy>methyl>bicyclo<5.3.0>dec-2-en-6-one

cis,anti, cis-1-methoxy-7-methyl-endo-3-<<(tert-butyldiphenylsilyl)oxy>methyl>tricyclo<5.3.0.0^2.6>decan-endo-8-ol

Toluene-4-sulfonic acid (1S,3aR,3bS,4R,6aS,6bS)-4-(tert-butyl-dimethyl-silanyloxymethyl)-3a-methoxy-6b-methyl-decahydro-cyclobutadicyclopenten-1-yl ester

cis-2-methyl-endo-8-<<(tert-butyldiphenylsilyl)oxy>methyl>-endo-5-(carbethoxymethyl)bicyclo<5.3.0>dec-2-en-6-one