methyl (E)-(3R^*,4S^*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate

Base Information

• Chemical Name: methyl (E)-(3R^*,4S^*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate
• CAS No.: 88155-83-3
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• Mol file: 88155-83-3.mol

Synonyms:methyl (E)-(3R^*,4S^*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate

Chemical Property of methyl (E)-(3R^*,4S^*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (E)-(3R^*,4S^*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate

There total 22 articles about methyl (E)-(3R^*,4S^*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate 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: 98.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + (E)-(3R,4S)-4-Methoxy-3-methyl-6-phenyl-hex-5-enoic acid (88088-56-6,90695-46-8,90695-54-8) → methyl (E)-(3R*,4S*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate (88155-83-3)

Guidance literature:

In diethyl ether;

DOI:10.1246/cl.1983.1379

Reference yield:

(E)-(3S*,4R*)-3-methoxy-4-methyl-1-phenylhexa-1,5-diene (88088-54-4,106315-62-2,109864-19-9,109864-32-6) → methyl (E)-(3R*,4S*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate (88155-83-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) 9-BBN, 2.) 15percent aq. NaOH, 30percent aq. H₂O₂ / 1.) THF, from 0 deg C to RT, overnight, 2.) THF, EtOH, 4 h

2: 100 percent / 8 N Jones reagent / acetone / 2 h

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; jones reagent; dihydrogen peroxide; In acetone;

DOI:10.1021/jo00228a028

Reference yield:

(3S,4R)-4-Methyl-hex-5-en-1-yn-3-ol (79705-07-0,79705-08-1,88088-46-4,88088-47-5) → methyl (E)-(3R*,4S*)-4-methoxy-3-methyl-6-phenylhexa-5-enoate (88155-83-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 80 percent / CuI / (Ph₃P)2PdCl₂ / diethylamine / 10 h / 50 °C / Irradiation

2: 80 percent / LiAlH₄ / tetrahydrofuran / 3 h / Heating

3: 80 percent / NaH / tetrahydrofuran / 20 - 25 °C

4: 1.) 9-BBN; 2.) 3N NaOH, 30percent H₂O₂ / 1.) THF, 1.5 h at 0 deg C; 2.) at 5-10 deg C

5: PtO₂, NaHCO₃, O₂ / H₂O / 50 h / 90 - 100 °C

6: 87 percent / diethyl ether

With platinum(IV) oxide; sodium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; oxygen; sodium hydride; sodium hydrogencarbonate; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; diethyl ether; water; diethylamine;

DOI:10.1016/0040-4020(84)80013-7

upstream raw materials:

diazomethane

(E)-(3R,4S)-4-Methoxy-3-methyl-6-phenyl-hex-5-enoic acid

dibromomethyllithium

(E)-(2S,3R)-3-Methoxy-2-methyl-5-phenyl-pent-4-enoic acid methyl ester

Downstream raw materials:

oudemansin A

(+/-)-oudemansin A

(E)-(3S,4S)-2-Formyl-4-methoxy-3-methyl-6-phenyl-hex-5-enoic acid methyl ester

(E)-(3S,4S)-2-[1-Hydroxy-meth-(Z)-ylidene]-4-methoxy-3-methyl-6-phenyl-hex-5-enoic acid methyl ester