(5R,8S)-9,10-dihydroxy-8-{(1S)-1-hydroxy-2-[(4-methylphenyl)-(R)-sulfinyl]ethyl}-4,4,5-trimethyl-5,8-dihydro-1(4H)-anthracenone

Base Information

Chemical Name:(5R,8S)-9,10-dihydroxy-8-{(1S)-1-hydroxy-2-[(4-methylphenyl)-(R)-sulfinyl]ethyl}-4,4,5-trimethyl-5,8-dihydro-1(4H)-anthracenone
CAS No.:1417799-00-8
Molecular Formula:C₂₆H₂₈O₅S
Molecular Weight:452.571
Hs Code.:

Synonyms:(5R,8S)-9,10-dihydroxy-8-{(1S)-1-hydroxy-2-[(4-methylphenyl)-(R)-sulfinyl]ethyl}-4,4,5-trimethyl-5,8-dihydro-1(4H)-anthracenone

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Chemical Property of (5R,8S)-9,10-dihydroxy-8-{(1S)-1-hydroxy-2-[(4-methylphenyl)-(R)-sulfinyl]ethyl}-4,4,5-trimethyl-5,8-dihydro-1(4H)-anthracenone

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Technology Process of (5R,8S)-9,10-dihydroxy-8-{(1S)-1-hydroxy-2-[(4-methylphenyl)-(R)-sulfinyl]ethyl}-4,4,5-trimethyl-5,8-dihydro-1(4H)-anthracenone

There total 2 articles about (5R,8S)-9,10-dihydroxy-8-{(1S)-1-hydroxy-2-[(4-methylphenyl)-(R)-sulfinyl]ethyl}-4,4,5-trimethyl-5,8-dihydro-1(4H)-anthracenone 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:

: (1R,2S)-1-(p-tolylsulfinyl)-3,5-heptadien-2-ol

: 82208-38-6
8,8-dimethylnaphthalene-1,4,5(8H)-trione

: 1417798-95-8
(5S,8R)-9,10-dihydroxy-8-{(1S)-1-hydroxy-2-[(4-methylphenyl)-(R)-sulfinyl]ethyl}-4,4,5-trimethyl-5,8-dihydro-1(4H)-anthracenone

: 9,10-dihydroxy-5-{(1S)-1-hydroxy-2-[(4-methylphenyl)-(R)-sulfinyl]ethyl}-4,4,8-trimethyl-5,8-dihydro-1(4H)-anthracenone

: 1417799-00-8
(5R,8S)-9,10-dihydroxy-8-{(1S)-1-hydroxy-2-[(4-methylphenyl)-(R)-sulfinyl]ethyl}-4,4,5-trimethyl-5,8-dihydro-1(4H)-anthracenone

Guidance literature:: (1R,2S)-1-(p-tolylsulfinyl)-3,5-heptadien-2-ol; 8,8-dimethylnaphthalene-1,4,5(8H)-trione; In benzene; at 20 ℃; for 168h; Inert atmosphere; Darkness;

With silica gel; In benzene; at 20 ℃; Overall yield = 84 %; diastereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2012.11.017

Reference yield:

: (R)-1-(p-tolylsulfinyl)-3,5-heptadien-2-one

: 1417798-95-8
(5S,8R)-9,10-dihydroxy-8-{(1S)-1-hydroxy-2-[(4-methylphenyl)-(R)-sulfinyl]ethyl}-4,4,5-trimethyl-5,8-dihydro-1(4H)-anthracenone

: 9,10-dihydroxy-5-{(1S)-1-hydroxy-2-[(4-methylphenyl)-(R)-sulfinyl]ethyl}-4,4,8-trimethyl-5,8-dihydro-1(4H)-anthracenone

: 1417799-00-8
(5R,8S)-9,10-dihydroxy-8-{(1S)-1-hydroxy-2-[(4-methylphenyl)-(R)-sulfinyl]ethyl}-4,4,5-trimethyl-5,8-dihydro-1(4H)-anthracenone

Guidance literature:: Multi-step reaction with 2 steps

1.1: diisobutylaluminium hydride / tetrahydrofuran / -78 °C

2.1: benzene / 168 h / 20 °C / Inert atmosphere; Darkness

2.2: 20 °C / Inert atmosphere

With diisobutylaluminium hydride; In tetrahydrofuran; benzene; 2.1: |Diels-Alder Cycloaddition;
DOI:10.1016/j.tetasy.2012.11.017