(5S)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one

Base Information

• Chemical Name: (5S)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one
• CAS No.: 753497-69-7
• Molecular Formula: C₁₉H₂₃BrO₃
• Molecular Weight: 379.294
• Mol file: 753497-69-7.mol

Synonyms:(5S)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one

Chemical Property of (5S)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one

There total 1 articles about (5S)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one 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:

2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one → (5R)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one (753497-67-5) + (5S)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one (753497-69-7)

Guidance literature:

With bromine; In dichloromethane; for 0.4h;

DOI:10.1039/b404016c

Reference yield: 43.0%

methyl 4-formylbenzoate (1571-08-0) + (5S)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one (753497-69-7) → 4-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]-5(R)non-8-en-6-ylidenemethyl]-benzoic acid methyl ester (753497-85-7)

Guidance literature:

(5S)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.25h;

methyl 4-formylbenzoate; In tetrahydrofuran; at -78 ℃; for 0.5h;

With pyridine; dmap; acetic anhydride; at 80 ℃; for 1.5h;

DOI:10.1039/b404016c

Reference yield:

(5S)-8-bromo-2,2-dimethyl-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]non-8-en-7-one (753497-69-7) → 4(E)-[4-bromo-2(R)-hydroxy-(1(R)-hydroxy-5-phenylpentyl)-5-oxo-cyclopent-3-enylidenemethyl]-benzoic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

1.2: tetrahydrofuran / 0.5 h / -78 °C

1.3: 43 percent / Ac₂O; 4-DMAP; pyridine / 1.5 h / 80 °C

2.1: 46 percent / aq. TFA / tetrahydrofuran / 1 h / 20 °C

With trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1039/b404016c

Downstream raw materials:

4-[8-bromo-2,2-dimethyl-7-oxo-4(R)-(4-phenyl-butyl)-1,3-dioxaspiro[4.4]-5(R)non-8-en-6-ylidenemethyl]-benzoic acid methyl ester