(R)-3-((S)-acetoxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)but-3-en-2-yl benzoate

Base Information

• Chemical Name: (R)-3-((S)-acetoxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)but-3-en-2-yl benzoate
• CAS No.: 1265883-47-3
• Molecular Formula: C₃₅H₄₆O₈
• Molecular Weight: 594.745

Synonyms:(R)-3-((S)-acetoxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)but-3-en-2-yl benzoate

Chemical Property of (R)-3-((S)-acetoxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)but-3-en-2-yl benzoate

Chemical Property:

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Technology Process of (R)-3-((S)-acetoxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)but-3-en-2-yl benzoate

There total 20 articles about (R)-3-((S)-acetoxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)but-3-en-2-yl benzoate 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: 69.0%

(R)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)-3-((S)-hydroxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)but-3-en-2-yl benzoate (1265883-43-9) + acetic anhydride (108-24-7) → (R)-3-((S)-acetoxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)but-3-en-2-yl benzoate (1265883-47-3)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo102033h

Reference yield:

(+)-(3S)-N-methoxy-N,3-dimethylpent-4-enamide (1062292-02-7) → (R)-3-((S)-acetoxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)but-3-en-2-yl benzoate (1265883-47-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 5 h / Inert atmosphere; Reflux

3.1: bromine; triethylamine / dichloromethane / 2.08 h / 0 - 20 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / benzene / 10 h / Inert atmosphere; Reflux

5.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

5.2: 1 h / -78 °C / Inert atmosphere

6.1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; n-butyllithium; bromine; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane; benzene;

DOI:10.1021/jo102033h

Reference yield:

(S)-ethyl 3-methylpent-4-enoate (1265883-49-5) → (R)-3-((S)-acetoxy((S)-8-methyl-1,4-dioxaspiro[4.4]non-6-en-6-yl)methyl)-1-((1S,3R)-3-((E)-3-tert-butoxy-2-methyl-3-oxoprop-1-enyl)-2,2-dimethylcyclopropyl)but-3-en-2-yl benzoate (1265883-47-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: isopropylmagnesium chloride / tetrahydrofuran; diethyl ether / 0.5 h / -10 °C / Inert atmosphere

2.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 5 h / Inert atmosphere; Reflux

4.1: bromine; triethylamine / dichloromethane / 2.08 h / 0 - 20 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / benzene / 10 h / Inert atmosphere; Reflux

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

6.2: 1 h / -78 °C / Inert atmosphere

7.1: pyridine; dmap / dichloromethane / 0 - 20 °C / Inert atmosphere

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; n-butyllithium; bromine; isopropylmagnesium chloride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene;

DOI:10.1021/jo102033h

upstream raw materials:

(+)-(3S)-N-methoxy-N,3-dimethylpent-4-enamide

ethyl (3S)-3-methyl-4-oxobutanoate

(S)-ethyl 3-methylpent-4-enoate

C₈H₁₂O

Downstream raw materials:

C₃₃H₄₂O₇

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