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

Base Information

• Chemical Name: cis,anti, cis-1-methoxy-7-methyl-endo-3-<<(tert-butyldiphenylsilyl)oxy>methyl>tricyclo<5.3.0.0^2.6>decan-endo-8-ol
• CAS No.: 109306-78-7
• Molecular Formula: C₂₉H₄₀O₃Si
• Molecular Weight: 464.72

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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

There total 6 articles about cis,anti, cis-1-methoxy-7-methyl-endo-3-<<(tert-butyldiphenylsilyl)oxy>methyl>tricyclo<5.3.0.0^2.6>decan-endo-8-ol 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: 76.0%

(1S,3aR,3bS,4R,6aS,6bS)-4-Hydroxymethyl-3a-methoxy-6b-methyl-decahydro-cyclobutadicyclopenten-1-ol (109306-76-5) + tert-butylchlorodiphenylsilane (58479-61-1) → cis,anti, cis-1-methoxy-7-methyl-endo-3-<<(tert-butyldiphenylsilyl)oxy>methyl>tricyclo<5.3.0.02.6>decan-endo-8-ol (109306-78-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 12h;

DOI:10.1021/jo00392a019

Reference yield:

3-methoxy-2-methylcyclopent-2-enone (3883-56-5) → cis,anti, cis-1-methoxy-7-methyl-endo-3-<<(tert-butyldiphenylsilyl)oxy>methyl>tricyclo<5.3.0.02.6>decan-endo-8-ol (109306-78-7)

Guidance literature:

Multi-step reaction with 6 steps

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

3: 98 percent / H₂ / 5percent Pd/C / methanol / 60 h

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

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

6: 76 percent / (C₂H₅)3N, DMAP / CH₂Cl₂ / 12 h

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

DOI:10.1021/jo00392a019

Reference yield:

1-methyl-5-methoxybicyclo<3.2.0>hept-6-en-endo-2-ol (109306-60-7) → cis,anti, cis-1-methoxy-7-methyl-endo-3-<<(tert-butyldiphenylsilyl)oxy>methyl>tricyclo<5.3.0.02.6>decan-endo-8-ol (109306-78-7)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/jo00392a019

upstream raw materials:

(1S,3aR,3bS,4R,6aS,6bS)-4-Hydroxymethyl-3a-methoxy-6b-methyl-decahydro-cyclobutadicyclopenten-1-ol

tert-butylchlorodiphenylsilane

3-methoxy-2-methylcyclopent-2-enone

1-methyl-5-methoxybicyclo<3.2.0>hept-6-en-endo-2-ol

Downstream raw materials:

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

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

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

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