(1R,2R,6S,8S,10R,11S)-11-Allyl-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-ene

Base Information

• Chemical Name: (1R,2R,6S,8S,10R,11S)-11-Allyl-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-ene
• CAS No.: 349649-00-9
• Molecular Formula: C₃₃H₅₀O₃Si₂
• Molecular Weight: 550.929
• Mol file: 349649-00-9.mol

Synonyms:(1R,2R,6S,8S,10R,11S)-11-Allyl-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-ene

Chemical Property of (1R,2R,6S,8S,10R,11S)-11-Allyl-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,6S,8S,10R,11S)-11-Allyl-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-ene

There total 4 articles about (1R,2R,6S,8S,10R,11S)-11-Allyl-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.0^1,6]dodec-4-ene 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: 79.0%

(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-((Z)-(R)-4-iodo-1-methyl-but-3-enyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-ene (349648-87-9) → (1R,2R,6S,8S,10R,11S)-11-Allyl-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.01,6]dodec-4-ene (349649-00-9)

Guidance literature:

With tetrabutylammomium bromide; potassium formate; palladium diacetate; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1021/ja010643u

Reference yield:

(R)-3-{3-[(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-butyryl}-4-phenyl-oxazolidin-2-one → (1R,2R,6S,8S,10R,11S)-11-Allyl-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.01,6]dodec-4-ene (349649-00-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / LiBH₄; methanol / tetrahydrofuran / 1 h / 0 °C

2: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 0.67 h / -78 °C

3: 657 mg / sodium hexamethyldisilazide; HMPA / tetrahydrofuran / 0.58 h / -78 - -30 °C

4: 79 percent / n-Bu₄NBr; HCO₂K / Pd(OAc)2 / dimethylformamide / 24 h / 20 °C

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium borohydride; oxalyl dichloride; tetrabutylammomium bromide; potassium formate; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; palladium diacetate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: Swern oxidation / 4: Heck reaction;

DOI:10.1021/ja010643u

Reference yield:

(R)-3-[(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-butan-1-ol (349649-08-7) → (1R,2R,6S,8S,10R,11S)-11-Allyl-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-phenylethynyl-10-trimethylsilanyloxy-12-oxa-tricyclo[6.3.1.01,6]dodec-4-ene (349649-00-9)

Guidance literature:

Multi-step reaction with 3 steps

1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 0.67 h / -78 °C

2: 657 mg / sodium hexamethyldisilazide; HMPA / tetrahydrofuran / 0.58 h / -78 - -30 °C

3: 79 percent / n-Bu₄NBr; HCO₂K / Pd(OAc)2 / dimethylformamide / 24 h / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; tetrabutylammomium bromide; potassium formate; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; palladium diacetate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Swern oxidation / 3: Heck reaction;

DOI:10.1021/ja010643u

upstream raw materials:

(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-1-((Z)-(R)-4-iodo-1-methyl-but-3-enyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-ene

(R)-3-[(1R,2S,3R,5R)-2-Allyl-5-(tert-butyl-dimethyl-silanyloxymethyl)-3-phenylethynyl-3-trimethylsilanyloxy-8-oxa-bicyclo[3.2.1]oct-6-en-1-yl]-butan-1-ol

Downstream raw materials:

C₃₃H₅₂O₃Si₂

C₃₃H₅₂O₄Si₂