(3S,5R,6S)-1-((4-methoxybenzyl)oxy)-5-(methoxymethoxy)-6-methylnon-8-en-3-ol

Base Information

• Chemical Name: (3S,5R,6S)-1-((4-methoxybenzyl)oxy)-5-(methoxymethoxy)-6-methylnon-8-en-3-ol
• CAS No.: 1298015-35-6
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.471

Synonyms:(3S,5R,6S)-1-((4-methoxybenzyl)oxy)-5-(methoxymethoxy)-6-methylnon-8-en-3-ol

Chemical Property of (3S,5R,6S)-1-((4-methoxybenzyl)oxy)-5-(methoxymethoxy)-6-methylnon-8-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (3S,5R,6S)-1-((4-methoxybenzyl)oxy)-5-(methoxymethoxy)-6-methylnon-8-en-3-ol

There total 7 articles about (3S,5R,6S)-1-((4-methoxybenzyl)oxy)-5-(methoxymethoxy)-6-methylnon-8-en-3-ol 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: 95.0%

(5R,7S)-9,9-diisopropyl-7-(2-((4-methoxybenzyl)oxy)ethyl)-10-methyl-5-((S)-pent-4-en-2-yl)-2,4,8-trioxa-9-silaundecane (1298015-34-5) → (3S,5R,6S)-1-((4-methoxybenzyl)oxy)-5-(methoxymethoxy)-6-methylnon-8-en-3-ol (1298015-35-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo200337v

Reference yield:

(4S,E)-4-((4R,6S)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)-ethyl)-2-oxido-1,3,2-dioxaphosphinan-4-yl)pent-2-en-1-yl acetate (1298015-31-2) → (3S,5R,6S)-1-((4-methoxybenzyl)oxy)-5-(methoxymethoxy)-6-methylnon-8-en-3-ol (1298015-35-6)

Guidance literature:

Multi-step reaction with 5 steps

1: ammonium formate; palladium diacetate; triphenylphosphine / 1,2-dichloro-ethane / 1 h / 90 °C / Inert atmosphere

2: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C / Inert atmosphere

3: 2,6-dimethylpyridine / dichloromethane / -78 - 0 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; ammonium formate; palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jo200337v

Reference yield:

(4R,6S)-4-((S)-but-3-en-2-yl)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)ethyl)-1,3,2-dioxaphosphinane 2-oxide (1298015-30-1) → (3S,5R,6S)-1-((4-methoxybenzyl)oxy)-5-(methoxymethoxy)-6-methylnon-8-en-3-ol (1298015-35-6)

Guidance literature:

Multi-step reaction with 6 steps

1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 1 h / 45 °C / Inert atmosphere

2: ammonium formate; palladium diacetate; triphenylphosphine / 1,2-dichloro-ethane / 1 h / 90 °C / Inert atmosphere

3: lithium aluminium tetrahydride / diethyl ether / 1 h / 0 °C / Inert atmosphere

4: 2,6-dimethylpyridine / dichloromethane / -78 - 0 °C / Inert atmosphere

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; Hoveyda-Grubbs catalyst second generation; tetrabutyl ammonium fluoride; ammonium formate; palladium diacetate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jo200337v

upstream raw materials:

(4R,6S)-4-((S)-but-3-en-2-yl)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)ethyl)-1,3,2-dioxaphosphinane 2-oxide

(4S,E)-4-((4R,6S)-2-methoxy-6-(2-((4-methoxybenzyl)oxy)-ethyl)-2-oxido-1,3,2-dioxaphosphinan-4-yl)pent-2-en-1-yl acetate

(4S,6R)-2-methoxy-4-(2-((4-methoxybenzyl)oxy)ethyl)-6-((S)-pent-4-en-2-yl)-1,3,2-dioxaphosphinane 2-oxide

(3S,5R,6S)-1-((4-methoxybenzyl)oxy)-6-methylnon-8-ene-3,5-diol

Downstream raw materials:

(3S,5R,6S,Z)-14-methoxy-3-(2-((4-methoxybenzyl)oxy)-ethyl)-5-(methoxymethoxy)-6-methyl-3,4,5,6,7,10-hexahydro-1H-benzo[c][1]oxacyclododecin-1-one

(3S,5R,6S,E)-14-methoxy-3-(2-((4-methoxybenzyl)oxy)-ethyl)-5-(methoxymethoxy)-6-methyl-3,4,5,6,7,10-hexahydro-1H-benzo[c][1]oxacyclododecin-1-one

2-methoxy-6-(prop-2-enyl)benzoic acid (1S,3R,4S)-1-[2-(4-methoxybenzyloxy)ethyl]-3-methoxymethoxy-4-methylhept-6-enyl ester

(3S,5R,6S)-1-((4-methoxybenzyl)oxy)-5-(methoxymethoxy)-6-methylnon-8-en-3-yl 2-allyl-6-hydroxybenzoate

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