(3S,5R)-2-hydroxy-2-methyl-5-(4-methyl-3,6-dioxocyclohexa-1,4-dienyl)hept-6-en-3-yl acetate

Base Information

• Chemical Name: (3S,5R)-2-hydroxy-2-methyl-5-(4-methyl-3,6-dioxocyclohexa-1,4-dienyl)hept-6-en-3-yl acetate
• CAS No.: 1398247-54-5
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359

Synonyms:(3S,5R)-2-hydroxy-2-methyl-5-(4-methyl-3,6-dioxocyclohexa-1,4-dienyl)hept-6-en-3-yl acetate

Chemical Property of (3S,5R)-2-hydroxy-2-methyl-5-(4-methyl-3,6-dioxocyclohexa-1,4-dienyl)hept-6-en-3-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5R)-2-hydroxy-2-methyl-5-(4-methyl-3,6-dioxocyclohexa-1,4-dienyl)hept-6-en-3-yl acetate

There total 12 articles about (3S,5R)-2-hydroxy-2-methyl-5-(4-methyl-3,6-dioxocyclohexa-1,4-dienyl)hept-6-en-3-yl acetate 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:

1,4-dimethoxy-2-methyl-5-(2-methylbut-3-en-2-yloxy)-benzene (1398242-98-2) → (3S,5R)-2-hydroxy-2-methyl-5-(4-methyl-3,6-dioxocyclohexa-1,4-dienyl)hept-6-en-3-yl acetate (1398247-54-5) + (3S,5S)-2-hydroxy-2-methyl-5-(4-methyl-3,6-dioxocyclohexa-1,4-dienyl)hept-6-en-3-yl acetate (1398247-88-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; potassium hexacyanoferrate(III); potassium carbonate; potassium osmate monohydrate; methanesulfonamide / water; tert-butyl alcohol / 19 h / 0 °C

2.1: triethylamine; dmap / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

3.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

4.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: 0.17 h / -78 °C / Inert atmosphere

4.3: 1 h / -78 °C / Inert atmosphere

5.1: quinoline; hydrogen / ethyl acetate / 1 h / 50 °C

6.1: dmap; pyridine / dichloromethane / 5.5 h / 20 °C

7.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.08 h / 0 °C

8.1: t-butyldimethylsiyl triflate / 0.5 h / -10 °C / Inert atmosphere

With pyridine; quinoline; dmap; n-butyllithium; ammonium cerium (IV) nitrate; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; methanesulfonamide; potassium osmate monohydrate; potassium hexacyanoferrate(III); t-butyldimethylsiyl triflate; hydrogen; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; acetonitrile; tert-butyl alcohol; 8.1: |Hosomi-Sakurai Reaction;

DOI:10.1021/jo3016055

Reference yield:

(S,Z)-2-(2,5-dimethoxy-4-methylphenoxy)-2-methyl-7-(trimethylsilyl)hept-5-en-3-ol (1398243-28-1) → (3S,5R)-2-hydroxy-2-methyl-5-(4-methyl-3,6-dioxocyclohexa-1,4-dienyl)hept-6-en-3-yl acetate (1398247-54-5) + (3S,5S)-2-hydroxy-2-methyl-5-(4-methyl-3,6-dioxocyclohexa-1,4-dienyl)hept-6-en-3-yl acetate (1398247-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; pyridine / dichloromethane / 5.5 h / 20 °C

2: ammonium cerium (IV) nitrate / water; acetonitrile / 0.08 h / 0 °C

3: t-butyldimethylsiyl triflate / 0.5 h / -10 °C / Inert atmosphere

With pyridine; dmap; ammonium cerium (IV) nitrate; t-butyldimethylsiyl triflate; In dichloromethane; water; acetonitrile; 3: |Hosomi-Sakurai Reaction;

DOI:10.1021/jo3016055

Reference yield:

(S)-2-(2,5-dimethoxy-4-methylphenoxy)-2-methyl-7-(trimethylsilyl)hept-5-yn-3-ol (1398244-40-0) → (3S,5R)-2-hydroxy-2-methyl-5-(4-methyl-3,6-dioxocyclohexa-1,4-dienyl)hept-6-en-3-yl acetate (1398247-54-5) + (3S,5S)-2-hydroxy-2-methyl-5-(4-methyl-3,6-dioxocyclohexa-1,4-dienyl)hept-6-en-3-yl acetate (1398247-88-5)

Guidance literature:

Multi-step reaction with 4 steps

1: quinoline; hydrogen / ethyl acetate / 1 h / 50 °C

2: dmap; pyridine / dichloromethane / 5.5 h / 20 °C

3: ammonium cerium (IV) nitrate / water; acetonitrile / 0.08 h / 0 °C

4: t-butyldimethylsiyl triflate / 0.5 h / -10 °C / Inert atmosphere

With pyridine; quinoline; dmap; ammonium cerium (IV) nitrate; t-butyldimethylsiyl triflate; hydrogen; In dichloromethane; water; ethyl acetate; acetonitrile; 4: |Hosomi-Sakurai Reaction;

DOI:10.1021/jo3016055

upstream raw materials:

1,4-dimethoxy-2-methyl-5-(2-methylbut-3-en-2-yloxy)-benzene

(S)-3-(2,5-dimethoxy-4-methylphenoxy)-3-methylbutane-1,2-diol

2,5-dimethoxy-4-methylbenzaldehyde

(S)-3-(2,5-dimethoxy-4-methylphenoxy)-2-hydroxy-3-methylbutyl 4-methylbenzenesulfonat

Downstream raw materials:

(3S,5R)-5-(2,5-dihydroxy-4-methylphenyl)-2-hydroxy-2-methylhept-6-en-3-yl acetate

(3S,5R)-2-(2,3-dihydroxy-2-methylhept-6-en-5-yl)-5-methylbenzene-1,4-diol

(3S,5R)-2-(2,3-dihydroxy-2-methylhept-6-en-5-yl)-5-methylcyclohexa-2,5-diene-1,4-dione

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