(1R,3R,8R,9R,10S)-(+)-9-(3,4-dimethoxy-phenyl)-12,12-dimethoxy-3-(1-methyl-1-trimethylsilanyloxyethyl)-10-triisopropylsilanyloxy-4-oxa-tricyclo[6.3.1.0^1.5]dodec-5-en-7-one

Base Information

• Chemical Name: (1R,3R,8R,9R,10S)-(+)-9-(3,4-dimethoxy-phenyl)-12,12-dimethoxy-3-(1-methyl-1-trimethylsilanyloxyethyl)-10-triisopropylsilanyloxy-4-oxa-tricyclo[6.3.1.0^1.5]dodec-5-en-7-one
• CAS No.: 945553-71-9
• Molecular Formula: C₃₆H₆₀O₈Si₂
• Molecular Weight: 677.039

Synonyms:(1R,3R,8R,9R,10S)-(+)-9-(3,4-dimethoxy-phenyl)-12,12-dimethoxy-3-(1-methyl-1-trimethylsilanyloxyethyl)-10-triisopropylsilanyloxy-4-oxa-tricyclo[6.3.1.0^1.5]dodec-5-en-7-one

Chemical Property of (1R,3R,8R,9R,10S)-(+)-9-(3,4-dimethoxy-phenyl)-12,12-dimethoxy-3-(1-methyl-1-trimethylsilanyloxyethyl)-10-triisopropylsilanyloxy-4-oxa-tricyclo[6.3.1.0^1.5]dodec-5-en-7-one

Chemical Property:

Purity/Quality:

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Technology Process of (1R,3R,8R,9R,10S)-(+)-9-(3,4-dimethoxy-phenyl)-12,12-dimethoxy-3-(1-methyl-1-trimethylsilanyloxyethyl)-10-triisopropylsilanyloxy-4-oxa-tricyclo[6.3.1.0^1.5]dodec-5-en-7-one

There total 4 articles about (1R,3R,8R,9R,10S)-(+)-9-(3,4-dimethoxy-phenyl)-12,12-dimethoxy-3-(1-methyl-1-trimethylsilanyloxyethyl)-10-triisopropylsilanyloxy-4-oxa-tricyclo[6.3.1.0^1.5]dodec-5-en-7-one 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:

C34H54O8Si + chloro-trimethyl-silane (75-77-4) → (1R,3R,8R,9R,10S)-(+)-9-(3,4-dimethoxy-phenyl)-12,12-dimethoxy-3-(1-methyl-1-trimethylsilanyloxyethyl)-10-triisopropylsilanyloxy-4-oxa-tricyclo[6.3.1.01.5]dodec-5-en-7-one (945553-71-9) + (1R,3S,8R,9R,10S)-(-)-9-(3,4-dimethoxy-phenyl)-12,12-dimethoxy-3-(1-methyl-1-trimethylsilanyloxyethyl)-10-triisopropylsilanyloxy-4-oxa-tricyclo[6.3.1.01.5]dodec-5-en-7-one

Guidance literature:

C₃₄H₅₄O₈Si; With chloro-trimethyl-silane; In dichloromethane; at 0 ℃; for 2h;

chloro-trimethyl-silane; With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 0 ℃; for 2h; Further stages.;

DOI:10.1039/b704311b

Reference yield:

(1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one (945553-45-7) → (1R,3R,8R,9R,10S)-(+)-9-(3,4-dimethoxy-phenyl)-12,12-dimethoxy-3-(1-methyl-1-trimethylsilanyloxyethyl)-10-triisopropylsilanyloxy-4-oxa-tricyclo[6.3.1.01.5]dodec-5-en-7-one (945553-71-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: DIPA*HCl; nBuLi / tetrahydrofuran; hexane / 3 h / -78 °C

1.2: 75 percent / tetrahydrofuran; hexane / 3 h / -78 °C

2.1: dimethyldioxirane / acetone; CH₂Cl₂ / 3.5 h / 0 °C

3.1: trimethylsilyl chloride / CH₂Cl₂ / 2 h / 0 °C

3.2: 70 mg / DMAP; imidazole / dimethylformamide / 2 h / 0 °C

With n-butyllithium; chloro-trimethyl-silane; 3,3-dimethyldioxirane; In tetrahydrofuran; hexane; dichloromethane; acetone;

DOI:10.1039/b704311b

Reference yield:

(1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-5-(prenyl)-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one (945553-47-9) → (1R,3R,8R,9R,10S)-(+)-9-(3,4-dimethoxy-phenyl)-12,12-dimethoxy-3-(1-methyl-1-trimethylsilanyloxyethyl)-10-triisopropylsilanyloxy-4-oxa-tricyclo[6.3.1.01.5]dodec-5-en-7-one (945553-71-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dimethyldioxirane / acetone; CH₂Cl₂ / 3.5 h / 0 °C

2.1: trimethylsilyl chloride / CH₂Cl₂ / 2 h / 0 °C

2.2: 70 mg / DMAP; imidazole / dimethylformamide / 2 h / 0 °C

With chloro-trimethyl-silane; 3,3-dimethyldioxirane; In dichloromethane; acetone;

DOI:10.1039/b704311b

upstream raw materials:

chloro-trimethyl-silane

(1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one

(1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-5-(prenyl)-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one

prenyl bromide

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