(-)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

Base Information

Chemical Name:(-)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one
CAS No.:1337985-33-7
Molecular Formula:C₃₃H₃₄ClNO₉Si
Molecular Weight:652.173
Hs Code.:

(-)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

Synonyms:(-)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

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Chemical Property of (-)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

Chemical Property:

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MSDS Files:: SDS file from LookChem

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Technology Process of (-)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

There total 3 articles about (-)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-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: 70.0%

: 1337985-30-4
(-)-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,10b-dihydrobenzo[c]phenanthridin-6(5H)-one

: 937-14-4
3-chloro-benzenecarboperoxoic acid

: 1337985-33-7
(-)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

Guidance literature:: In dichloromethane; at 0 - 20 ℃; for 27h; optical yield given as %ee; Inert atmosphere;
DOI:10.1016/j.tet.2011.07.091

Reference yield:

: 617-86-7
triethylsilane

: 1337985-33-7
(-)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

Guidance literature:: Multi-step reaction with 3 steps

1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -35 °C

2: potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 7 h / 85 °C / Inert atmosphere

3: dichloromethane / 27 h / 0 - 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; benzene; 2: Pinacol type rearrangement;
DOI:10.1016/j.tet.2011.07.091

Reference yield:

: 4b,10b-dihydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-4b,10b,11,12-tetrahydrobenzo[c]phenanthridin-6(5H)-one

: 1337985-33-7
(-)-12-(3-chlorobenzoyloxy)-11-hydroxy-5-methyl-2,3:7,8-bis(methylenedioxy)-10b-triethylsilyloxy-4b,5,6,10b,11,12-hexahydrobenzo[c]phenanthridin-6(5H)-one

Guidance literature:: Multi-step reaction with 3 steps

1: boron trifluoride diethyl etherate / dichloromethane / 2 h / -35 °C

2: potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 7 h / 85 °C / Inert atmosphere

3: dichloromethane / 27 h / 0 - 20 °C / Inert atmosphere

With boron trifluoride diethyl etherate; potassium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; benzene; 2: Pinacol type rearrangement;
DOI:10.1016/j.tet.2011.07.091