(2S,3R,5R,6R)-5-((S)-4-hydroxy-4-methyl-2-oxooct-7-enyl)-6-(4-methoxybenzyloxy)-2,3-dimethyl-2-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclohexanone

Base Information

Chemical Name:(2S,3R,5R,6R)-5-((S)-4-hydroxy-4-methyl-2-oxooct-7-enyl)-6-(4-methoxybenzyloxy)-2,3-dimethyl-2-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclohexanone
CAS No.:1260612-81-4
Molecular Formula:C₃₁H₄₆O₇
Molecular Weight:530.702
Hs Code.:

Synonyms:(2S,3R,5R,6R)-5-((S)-4-hydroxy-4-methyl-2-oxooct-7-enyl)-6-(4-methoxybenzyloxy)-2,3-dimethyl-2-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclohexanone

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Chemical Property of (2S,3R,5R,6R)-5-((S)-4-hydroxy-4-methyl-2-oxooct-7-enyl)-6-(4-methoxybenzyloxy)-2,3-dimethyl-2-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclohexanone

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Technology Process of (2S,3R,5R,6R)-5-((S)-4-hydroxy-4-methyl-2-oxooct-7-enyl)-6-(4-methoxybenzyloxy)-2,3-dimethyl-2-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclohexanone

There total 20 articles about (2S,3R,5R,6R)-5-((S)-4-hydroxy-4-methyl-2-oxooct-7-enyl)-6-(4-methoxybenzyloxy)-2,3-dimethyl-2-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclohexanone 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: 65.0%

: 1260612-79-0
(3S,4R,10S)-1-(4-methoxybenzyloxy)-3,4,10-trimethyl-3-(2-(2-methyl-(1,3)dioxolan-2-yl)ethyl)-10-triethylsilanyloxytetradeca-6,13-diene-2,8-dione

: 1260612-81-4
(2S,3R,5R,6R)-5-((S)-4-hydroxy-4-methyl-2-oxooct-7-enyl)-6-(4-methoxybenzyloxy)-2,3-dimethyl-2-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclohexanone

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1.5h;
DOI:10.1021/ol1026816

Reference yield:

: 1260612-73-4
(1R,5R)-1-ethyl 2-methyl 5-methyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclopent-2-ene-1,2-dicarboxylate

: 1260612-81-4
(2S,3R,5R,6R)-5-((S)-4-hydroxy-4-methyl-2-oxooct-7-enyl)-6-(4-methoxybenzyloxy)-2,3-dimethyl-2-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclohexanone

Guidance literature:: Multi-step reaction with 7 steps

1.1: diisobutylaluminium hydride / hexane / 4 h / -78 - 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

2.2: 15 h / 0 - 20 °C

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve

4.1: hydrazine / ethylene glycol / 0.5 h / 130 °C

4.2: 3 h / 230 °C

5.1: oxygen; ozone / dichloromethane / -78 °C

5.2: 3 h / -78 - 20 °C

6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C

6.2: 0.25 h / 0 °C

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C

With tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; oxygen; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; ozone; 4-methylmorpholine N-oxide; hydrazine; In tetrahydrofuran; hexane; dichloromethane; ethylene glycol; mineral oil; 4.2: Wolff-Kishner reduction / 6.2: Horner-Wadsworth-Emmons olefination / 7.1: Michael reaction;
DOI:10.1021/ol1026816

Reference yield:

: 1260612-72-3
(1R,5R)-ethyl 5-methyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-2-(trifluoromethylsulfonyloxy)cyclopent-2-enecarboxylate

: 1260612-81-4
(2S,3R,5R,6R)-5-((S)-4-hydroxy-4-methyl-2-oxooct-7-enyl)-6-(4-methoxybenzyloxy)-2,3-dimethyl-2-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclohexanone

Guidance literature:: Multi-step reaction with 8 steps

1.1: palladium diacetate; triethylamine; triphenylphosphine / N,N-dimethyl-formamide / 16 h / 45 °C / 760.05 Torr

2.1: diisobutylaluminium hydride / hexane / 4 h / -78 - 20 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

3.2: 15 h / 0 - 20 °C

4.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve

5.1: hydrazine / ethylene glycol / 0.5 h / 130 °C

5.2: 3 h / 230 °C

6.1: oxygen; ozone / dichloromethane / -78 °C

6.2: 3 h / -78 - 20 °C

7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C

7.2: 0.25 h / 0 °C

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C

With tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; oxygen; palladium diacetate; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; ozone; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; hydrazine; In tetrahydrofuran; hexane; dichloromethane; ethylene glycol; N,N-dimethyl-formamide; mineral oil; 5.2: Wolff-Kishner reduction / 7.2: Horner-Wadsworth-Emmons olefination / 8.1: Michael reaction;
DOI:10.1021/ol1026816