(4aR,5S,6R,8aR)-4a-hydroxy-8a-methyl-5-(4-nitrobenzoyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one

Base Information

• Chemical Name: (4aR,5S,6R,8aR)-4a-hydroxy-8a-methyl-5-(4-nitrobenzoyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one
• CAS No.: 1416969-96-4
• Molecular Formula: C₂₄H₃₂BNO₇
• Molecular Weight: 457.332
• Mol file: 1416969-96-4.mol

Synonyms:

Chemical Property of (4aR,5S,6R,8aR)-4a-hydroxy-8a-methyl-5-(4-nitrobenzoyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aR,5S,6R,8aR)-4a-hydroxy-8a-methyl-5-(4-nitrobenzoyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one

There total 2 articles about (4aR,5S,6R,8aR)-4a-hydroxy-8a-methyl-5-(4-nitrobenzoyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-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:

2-[(E)-5-(4-nitrophenyl)-5-oxopent-3-enyl]-2-methylcyclohexane-1,3-dione (1416969-82-8) + bis(pinacol)diborane (73183-34-3) → (4aR,5S,6R,8aR)-4a-hydroxy-8a-methyl-5-(4-nitrobenzoyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one (1416969-96-4) + (4aS,5S,6R,8aS)-4a-hydroxy-8a-methyl-5-(4-nitrobenzoyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one (1416969-97-5) + (4aS,5R,6S,8aS)-4a-hydroxy-8a-methyl-5-(4-nitrobenzoyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one + (4aR,5R,6S,8aR)-4a-hydroxy-8a-methyl-5-(4-nitrobenzoyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one

Guidance literature:

bis(pinacol)diborane; With (R)-1-[(S_P)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; copper(l) chloride; sodium t-butanolate; In tetrahydrofuran; at 20 ℃; for 0.5h;

2-[(E)-5-(4-nitrophenyl)-5-oxopent-3-enyl]-2-methylcyclohexane-1,3-dione; In tetrahydrofuran; isopropyl alcohol; at 20 ℃; for 18h; enantioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201205899

Reference yield:

1-(4-nitro-phenyl)-2-(triphenyl-λ5-phosphanylidene)-ethanone (1439-43-6) + 3-(2-methyl-1,3-dioxocyclohexyl)propionaldehyde (552855-46-6) → (4aR,5S,6R,8aR)-4a-hydroxy-8a-methyl-5-(4-nitrobenzoyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one (1416969-96-4) + (4aS,5S,6R,8aS)-4a-hydroxy-8a-methyl-5-(4-nitrobenzoyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one (1416969-97-5) + (4aS,5R,6S,8aS)-4a-hydroxy-8a-methyl-5-(4-nitrobenzoyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one + (4aR,5R,6S,8aR)-4a-hydroxy-8a-methyl-5-(4-nitrobenzoyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)octahydronaphthalen-1(2H)-one

Guidance literature:

Multi-step reaction with 2 steps

1.1: chloroform / 4 h / 20 °C / Inert atmosphere; Reflux

2.1: copper(l) chloride; sodium t-butanolate; (R)-1-[(S_P)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine / tetrahydrofuran / 0.5 h / 20 °C

2.2: 18 h / 20 °C / Inert atmosphere

With (R)-1-[(S_P)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; copper(l) chloride; sodium t-butanolate; In tetrahydrofuran; chloroform; 1.1: |Wittig Rearrangement;

DOI:10.1002/anie.201205899

upstream raw materials:

2-[(E)-5-(4-nitrophenyl)-5-oxopent-3-enyl]-2-methylcyclohexane-1,3-dione

bis(pinacol)diborane

1-(4-nitro-phenyl)-2-(triphenyl-λ⁵-phosphanylidene)-ethanone

3-(2-methyl-1,3-dioxocyclohexyl)propionaldehyde