(2S,3S)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-2-methyl-3-((3Z,7E)-4,8,12-trimethyl-trideca-3,7,11-trienyl)-oxirane

Base Information

• Chemical Name: (2S,3S)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-2-methyl-3-((3Z,7E)-4,8,12-trimethyl-trideca-3,7,11-trienyl)-oxirane
• CAS No.: 56882-07-6
• Molecular Formula: C₃₀H₅₀O
• Molecular Weight: 426.726
• Mol file: 56882-07-6.mol

Synonyms:

Chemical Property of (2S,3S)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-2-methyl-3-((3Z,7E)-4,8,12-trimethyl-trideca-3,7,11-trienyl)-oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-2-methyl-3-((3Z,7E)-4,8,12-trimethyl-trideca-3,7,11-trienyl)-oxirane

There total 12 articles about (2S,3S)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-2-methyl-3-((3Z,7E)-4,8,12-trimethyl-trideca-3,7,11-trienyl)-oxirane 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: 24.0%

(E)-(6,10-dimethyl-5,9-undecadien-2-ylidene)triphenylphosphorane (83732-41-6) + 3-[(2R,3S)-3-((E)-4,8-Dimethyl-nona-3,7-dienyl)-3-methyl-oxiranyl]-propionaldehyde (85431-79-4,121786-70-7) → (2S,3R)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-2-methyl-3-((3Z,7E)-4,8,12-trimethyl-trideca-3,7,11-trienyl)-oxirane (56882-07-6,60661-28-1,82729-38-2,85505-96-0,109009-55-4,118245-21-9) + (10R, 11R)-(+)-squalene-10, 11-epoxide (109009-55-4)

Guidance literature:

In tetrahydrofuran; 1.) -78 deg C, 40 min 2.) RT, 5 h;

DOI:10.1016/0040-4039(82)80144-5

Reference yield:

Farnesol (106-28-5) → (2S,3S)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-2-methyl-3-((3Z,7E)-4,8,12-trimethyl-trideca-3,7,11-trienyl)-oxirane (56882-07-6,60661-28-1,82729-38-2,85505-96-0,109009-55-4,118245-21-9)

Guidance literature:

Multi-step reaction with 6 steps

1: diethyl (-)-tartrate, t-butyl hydroperoxide / Ti(O-i-Pr)4 / CH₂Cl₂ / -50 - -45 °C

2: 96 percent / pyridine / 0 degC, 5.5 h then room temperature, 20 min

3: NaI / acetone / 10 h / Ambient temperature

4: 84 percent / i-Pr₂NH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 °C

5: 81 percent / i-Bu₂AlH / toluene; methanol / -110 °C

6: 1.) n-BuLi / 1.) THF/hexane, -78 degC, 30 min; 2.) THF, -78 degC, 40 min then room temperature

With pyridine; tert.-butylhydroperoxide; n-butyllithium; diethyl (2S,3S)-tartrate; diisobutylaluminium hydride; diisopropylamine; sodium iodide; titanium(IV) isopropylate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; acetone; toluene;

DOI:10.1016/S0040-4020(01)87533-5

Reference yield:

(2R,3R)-epoxyfarnesyl iodide (85431-78-3) → (2S,3S)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-2-methyl-3-((3Z,7E)-4,8,12-trimethyl-trideca-3,7,11-trienyl)-oxirane (56882-07-6,60661-28-1,82729-38-2,85505-96-0,109009-55-4,118245-21-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / i-Pr₂NH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 °C

2: 81 percent / i-Bu₂AlH / toluene; methanol / -110 °C

3: 1.) n-BuLi / 1.) THF/hexane, -78 degC, 30 min; 2.) THF, -78 degC, 40 min then room temperature

With n-butyllithium; diisobutylaluminium hydride; diisopropylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; toluene;

DOI:10.1016/S0040-4020(01)87533-5

upstream raw materials:

(E)-(6,10-dimethyl-5,9-undecadien-2-ylidene)triphenylphosphorane

3-[(2R,3S)-3-((E)-4,8-Dimethyl-nona-3,7-dienyl)-3-methyl-oxiranyl]-propionaldehyde

Farnesol

(2S,3S)-2-((E)-4,8-Dimethyl-nona-3,7-dienyl)-3-iodomethyl-2-methyl-oxirane