(3R,4S)-6-(4-methoxybenzyloxy)-3,4-dimethyl-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-oxohexanal

Base Information

Chemical Name:(3R,4S)-6-(4-methoxybenzyloxy)-3,4-dimethyl-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-oxohexanal
CAS No.:1260612-78-9
Molecular Formula:C₂₂H₃₂O₆
Molecular Weight:392.492
Hs Code.:

Synonyms:(3R,4S)-6-(4-methoxybenzyloxy)-3,4-dimethyl-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-oxohexanal

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Chemical Property of (3R,4S)-6-(4-methoxybenzyloxy)-3,4-dimethyl-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-oxohexanal

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Technology Process of (3R,4S)-6-(4-methoxybenzyloxy)-3,4-dimethyl-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-oxohexanal

There total 10 articles about (3R,4S)-6-(4-methoxybenzyloxy)-3,4-dimethyl-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-oxohexanal 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: 73.0%

: 1260612-77-8
2-(2-((1S,5R)-2-((4-methoxybenzyloxy)methyl)-1,5-dimethylcyclopent-2-enyl)ethyl)-2-methyl-1,3-dioxolane

: 1260612-78-9
(3R,4S)-6-(4-methoxybenzyloxy)-3,4-dimethyl-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-oxohexanal

Guidance literature:: 2-(2-((1S,5R)-2-((4-methoxybenzyloxy)methyl)-1,5-dimethylcyclopent-2-enyl)ethyl)-2-methyl-1,3-dioxolane; With oxygen; ozone; In dichloromethane; at -78 ℃;

With triphenylphosphine; In dichloromethane; at -78 - 20 ℃; for 3h;
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

: 1260612-78-9
(3R,4S)-6-(4-methoxybenzyloxy)-3,4-dimethyl-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-oxohexanal

Guidance literature:: Multi-step reaction with 5 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

With tetrapropylammonium perruthennate; oxygen; sodium hydride; diisobutylaluminium hydride; ozone; 4-methylmorpholine N-oxide; hydrazine; In tetrahydrofuran; hexane; dichloromethane; ethylene glycol; mineral oil; 4.2: Wolff-Kishner reduction;
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

: 1260612-78-9
(3R,4S)-6-(4-methoxybenzyloxy)-3,4-dimethyl-4-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)-5-oxohexanal

Guidance literature:: Multi-step reaction with 6 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

With tetrapropylammonium perruthennate; oxygen; palladium diacetate; 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;
DOI:10.1021/ol1026816