Acetic acid (1S,2R,3S,6R,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-3-yl ester

Base Information

• Chemical Name: Acetic acid (1S,2R,3S,6R,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-3-yl ester
• CAS No.: 193464-59-4
• Molecular Formula: C₃₅H₅₄O₅Si₂
• Molecular Weight: 610.982

Synonyms:Acetic acid (1S,2R,3S,6R,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-3-yl ester

Chemical Property of Acetic acid (1S,2R,3S,6R,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-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1S,2R,3S,6R,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-3-yl ester

There total 10 articles about Acetic acid (1S,2R,3S,6R,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-3-yl ester 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:

(1S,2R,3S)-1-[5-(tert-Butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-ene-1,3-diol (193464-56-1) → Acetic acid (1S,2R,3S,6R,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-3-yl ester (193464-59-4)

Guidance literature:

Multi-step reaction with 7 steps

2: 1.) VO(acac)2, t-BuOOH, 2.) DMAP / 1.) CH₂Cl₂, 2.) Py

3: 79 percent / DBU / acetonitrile

4: 95 percent / H₂ / Pd/C / ethyl acetate

6: 83 percent / diethyl ether

7: 1.) LiBr, 2.) HMPA / 1.) THF

With tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; bis(acetylacetonate)oxovanadium; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide; palladium on activated charcoal; In diethyl ether; ethyl acetate; acetonitrile;

DOI:10.1021/ja9706256

Reference yield:

(2S,3S)-3-[5-(tert-Butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-3-hydroxy-N-methoxy-2,N-dimethyl-propionamide (193464-54-9) → Acetic acid (1S,2R,3S,6R,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-3-yl ester (193464-59-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 82 percent / tetrahydrofuran / 60 °C

2: 85 percent / DIBAL / tetrahydrofuran / -78 °C

4: 1.) VO(acac)2, t-BuOOH, 2.) DMAP / 1.) CH₂Cl₂, 2.) Py

5: 79 percent / DBU / acetonitrile

6: 95 percent / H₂ / Pd/C / ethyl acetate

8: 83 percent / diethyl ether

9: 1.) LiBr, 2.) HMPA / 1.) THF

With tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; bis(acetylacetonate)oxovanadium; hydrogen; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate; acetonitrile;

DOI:10.1021/ja9706256

Reference yield:

(1S,2S)-1-[5-(tert-Butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-1-hydroxy-2-methyl-hept-6-en-3-one (193464-55-0) → Acetic acid (1S,2R,3S,6R,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-3-yl ester (193464-59-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / DIBAL / tetrahydrofuran / -78 °C

3: 1.) VO(acac)2, t-BuOOH, 2.) DMAP / 1.) CH₂Cl₂, 2.) Py

4: 79 percent / DBU / acetonitrile

5: 95 percent / H₂ / Pd/C / ethyl acetate

7: 83 percent / diethyl ether

8: 1.) LiBr, 2.) HMPA / 1.) THF

With tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; bis(acetylacetonate)oxovanadium; hydrogen; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethyl acetate; acetonitrile;

DOI:10.1021/ja9706256

upstream raw materials:

chloro-trimethyl-silane

Acetic acid (1S,2R,3S,6R,8S,11S)-11-allyl-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-10-oxo-12-oxa-tricyclo[6.3.1.0^1,6]dodec-3-yl ester

lithium phenylacetylide

(1S,2R,3S)-1-[5-(tert-Butyl-dimethyl-silanyloxymethyl)-furan-2-yl]-2-methyl-hept-6-ene-1,3-diol

Downstream raw materials:

C₃₃H₅₄O₄Si₂

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