Acetic acid (R)-3-(4-benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-enyl ester

Base Information

• Chemical Name: Acetic acid (R)-3-(4-benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-enyl ester
• CAS No.: 603095-32-5
• Molecular Formula: C₂₄H₃₀O₃
• Molecular Weight: 366.5
• Mol file: 603095-32-5.mol

Synonyms:

Chemical Property of Acetic acid (R)-3-(4-benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (R)-3-(4-benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-enyl ester

There total 15 articles about Acetic acid (R)-3-(4-benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-enyl ester 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: 96.0%

acetic anhydride (108-24-7) + (R)-3-(4-Benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-en-1-ol (603095-52-9) → Acetic acid (R)-3-(4-benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-enyl ester (603095-32-5)

Guidance literature:

With pyridine;

DOI:10.1016/S0040-4039(03)01094-3

Reference yield:

3-(4-benzyloxy-3-methyl-phenyl)-pentanedioic acid dimethyl ester (532423-91-9) → Acetic acid (R)-3-(4-benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-enyl ester (603095-32-5)

Guidance literature:

Multi-step reaction with 15 steps

1: PLE / dimethylsulfoxide

2: BOP; Et₃N

3: LiBH₄ / diethyl ether; ethanol

4: CSA / benzene

5: DIBAL-H / benzene

6: BF₃*OEt₂

7: 99 percent / imidazole / dimethylformamide

8: MeI; NaHCO₃ / acetonitrile; H₂O

9: NaBH₄ / ethanol

10: 86 percent / pyridine

11: 98 percent / TBAF / tetrahydrofuran

12: SO₃*pyr; DMSO; Et₃N / CH₂Cl₂

13: K₂CO₃; MeOH

14: 91 percent / nBuLi / tetrahydrofuran

15: 96 percent / pyridine

With pyridine; 1H-imidazole; methanol; sodium tetrahydroborate; lithium borohydride; n-butyllithium; pyridine-SO₃ complex; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; dimethyl sulfoxide; triethylamine; methyl iodide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene; 14: Wittig reaction;

DOI:10.1016/S0040-4039(03)01094-3

Reference yield:

(S)-3-(4-Benzyloxy-3-methyl-phenyl)-5-hydroxy-pentanal → Acetic acid (R)-3-(4-benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-enyl ester (603095-32-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / nBuLi / tetrahydrofuran

2: 96 percent / pyridine

With pyridine; n-butyllithium; In tetrahydrofuran; 1: Wittig reaction;

DOI:10.1016/S0040-4039(03)01094-3

upstream raw materials:

acetic anhydride

(R)-3-(4-Benzyloxy-3-methyl-phenyl)-6-methyl-hept-5-en-1-ol

3-(4-benzyloxy-3-methyl-phenyl)-pentanedioic acid dimethyl ester

(R)-4-(4-Benzyloxy-3-methyl-phenyl)-tetrahydro-pyran-2-one

Downstream raw materials:

Acetic acid (S)-3-(3-bromo-4-hydroxy-5-methyl-phenyl)-5,6-dihydroxy-6-methyl-heptyl ester

Acetic acid (S)-5,6-dihydroxy-3-(4-hydroxy-3-methyl-phenyl)-6-methyl-heptyl ester

Acetic acid (S)-3-(4-benzyloxy-3-methyl-phenyl)-5,6-dihydroxy-6-methyl-heptyl ester

Refernces