(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

Base Information

• Chemical Name: (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
• CAS No.: 876748-97-9
• Molecular Formula: C₃₄H₄₈O₄Si
• Molecular Weight: 548.838

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Technology Process of (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

There total 7 articles about (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 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: 100.0%

(1R,2S,3S,4S,6R,7R,8R,9S)-4-Bromo-9-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3-hydroxy-6-isopropyl-3-methyl-12-oxa-tricyclo[6.3.1.02,7]dodecan-10-one (876748-96-8) → (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)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; at 80 ℃; for 3h;

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) → (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)

Guidance literature:

Multi-step reaction with 5 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

With 1H-imidazole; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); bis(cyclohexanyl)borane; water; tri-n-butyl-tin hydride; sodium methylate; 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) → (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)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jo052290d

upstream raw materials:

(1R,2S,3S,4S,6R,7R,8R,9S)-4-Bromo-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

(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

(1R,2R,6R,7R,8R,9S)-9-(3-Hydroxy-propyl)-6-isopropyl-3-methyl-12-oxa-tricyclo[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

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

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