Acetic acid (1R,2S,3R,6R,7R,8R,9S)-9-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-10-oxo-12-oxa-tricyclo[6.3.1.0^2,7]dodec-3-yl ester

Base Information

• Chemical Name: Acetic acid (1R,2S,3R,6R,7R,8R,9S)-9-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-10-oxo-12-oxa-tricyclo[6.3.1.0^2,7]dodec-3-yl ester
• CAS No.: 876748-80-0
• Molecular Formula: C₃₆H₅₀O₅Si
• Molecular Weight: 590.875

Synonyms:Acetic acid (1R,2S,3R,6R,7R,8R,9S)-9-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-10-oxo-12-oxa-tricyclo[6.3.1.0^2,7]dodec-3-yl ester

Chemical Property of Acetic acid (1R,2S,3R,6R,7R,8R,9S)-9-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-10-oxo-12-oxa-tricyclo[6.3.1.0^2,7]dodec-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of Acetic acid (1R,2S,3R,6R,7R,8R,9S)-9-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-10-oxo-12-oxa-tricyclo[6.3.1.0^2,7]dodec-3-yl ester

There total 8 articles about Acetic acid (1R,2S,3R,6R,7R,8R,9S)-9-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-10-oxo-12-oxa-tricyclo[6.3.1.0^2,7]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: 88.0%

(1R,2S,3R,6R,7R,8R,9S)-9-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-6-isopropyl-3-methyl-12-oxa-tricyclo[6.3.1.02,7]dodecan-10-one (876748-97-9) + acetic anhydride (108-24-7) → Acetic acid (1R,2S,3R,6R,7R,8R,9S)-9-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-10-oxo-12-oxa-tricyclo[6.3.1.02,7]dodec-3-yl ester (876748-80-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at -10 - 20 ℃; for 6h;

DOI:10.1021/jo052290d

Reference yield:

(1R,2R,6R,7R,8R,9R)-9-allyl-6-isopropyl-3-methyl-12-oxatricyclo[6.3.1.02,7]dodec-3-en-10-one (876748-94-6) → Acetic acid (1R,2S,3R,6R,7R,8R,9S)-9-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-10-oxo-12-oxa-tricyclo[6.3.1.02,7]dodec-3-yl ester (876748-80-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: NaOMe / methanol / Heating

2.1: dicyclohexylborane / tetrahydrofuran / 0.5 h / 20 °C

2.2: 65 percent / NaBO₃*H₂O / H₂O; tetrahydrofuran / 4 h / 20 °C

3.1: 100 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

4.1: 98 percent / H₂O; N-bromosuccinimide / tetrahydrofuran / 4 h / 20 °C

5.1: 100 percent / 2,2'-azobisisobutyronitrile; n-Bu₃SnH / benzene / 3 h / 80 °C

6.1: 88 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 6 h / -10 - 20 °C

With 1H-imidazole; dmap; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); bis(cyclohexanyl)borane; water; tri-n-butyl-tin hydride; sodium methylate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1021/jo052290d

Reference yield:

(1R,2R,6R,7R,8R,9S)-9-Allyl-6-isopropyl-3-methyl-12-oxa-tricyclo[6.3.1.02,7]dodec-3-en-10-one (876748-81-1) → Acetic acid (1R,2S,3R,6R,7R,8R,9S)-9-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-10-oxo-12-oxa-tricyclo[6.3.1.02,7]dodec-3-yl ester (876748-80-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dicyclohexylborane / tetrahydrofuran / 0.5 h / 20 °C

1.2: 65 percent / NaBO₃*H₂O / H₂O; tetrahydrofuran / 4 h / 20 °C

2.1: 100 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

3.1: 98 percent / H₂O; N-bromosuccinimide / tetrahydrofuran / 4 h / 20 °C

4.1: 100 percent / 2,2'-azobisisobutyronitrile; n-Bu₃SnH / benzene / 3 h / 80 °C

5.1: 88 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 6 h / -10 - 20 °C

With 1H-imidazole; dmap; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); bis(cyclohexanyl)borane; water; tri-n-butyl-tin hydride; triethylamine; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1021/jo052290d

upstream raw materials:

(1R,2S,3R,6R,7R,8R,9S)-9-[3-(tert-Butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-6-isopropyl-3-methyl-12-oxa-tricyclo[6.3.1.0^2,7]dodecan-10-one

acetic anhydride

(1R,2R,6R,7R,8R,9S)-9-Allyl-6-isopropyl-3-methyl-12-oxa-tricyclo[6.3.1.0^2,7]dodec-3-en-10-one

(1R,2R,6R,7R,8R,9R)-9-allyl-6-isopropyl-3-methyl-12-oxatricyclo[6.3.1.0^2,7]dodec-3-en-10-one

Downstream raw materials:

Acetic acid (1R,2S,3R,6R,7R,8R,9S)-9-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-6-isopropyl-3-methyl-11-oxo-10,13-dioxa-tricyclo[6.4.1.0^2,7]tridec-3-yl ester

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