(2E,6E)-9-((R)-3,3-Dimethyl-oxiranyl)-3,7-dimethyl-nona-2,6-dien-1-ol

Base Information

• Chemical Name: (2E,6E)-9-((R)-3,3-Dimethyl-oxiranyl)-3,7-dimethyl-nona-2,6-dien-1-ol
• CAS No.: 24163-91-5
• Molecular Formula: C₁₅H₂₆O₂
• Molecular Weight: 238.37
• Mol file: 24163-91-5.mol

Synonyms:

Chemical Property of (2E,6E)-9-((R)-3,3-Dimethyl-oxiranyl)-3,7-dimethyl-nona-2,6-dien-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,6E)-9-((R)-3,3-Dimethyl-oxiranyl)-3,7-dimethyl-nona-2,6-dien-1-ol

There total 6 articles about (2E,6E)-9-((R)-3,3-Dimethyl-oxiranyl)-3,7-dimethyl-nona-2,6-dien-1-ol 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: 87.0%

C17H30O4 → (2E,6E)-9-((R)-3,3-Dimethyl-oxiranyl)-3,7-dimethyl-nona-2,6-dien-1-ol (5233-98-7,5233-99-8,24163-90-4,24163-91-5,28444-34-0,34175-50-3,34175-53-6,37133-75-8,54984-01-9)

Guidance literature:

C₁₇H₃₀O₄; With pyridine; methanesulfonyl chloride; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere;

With potassium carbonate; In methanol; dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.202104014

Reference yield: 76.0%

(S)-9-(3,3-dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dienal → (S)-9-(3,3-dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dien-1-ol (5233-98-7,5233-99-8,24163-90-4,24163-91-5,28444-34-0,34175-50-3,34175-53-6,37133-75-8,54984-01-9) + (S,2E,6E)-9-(3,3-dimethyloxiran-2-yl)-3,7-dimethylnona-2,6-dien-1-ol (34175-53-6)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/acs.orglett.0c00935

Reference yield:

farnesyl acetate (29548-30-9) → (2E,6E)-9-((R)-3,3-Dimethyl-oxiranyl)-3,7-dimethyl-nona-2,6-dien-1-ol (5233-98-7,5233-99-8,24163-90-4,24163-91-5,28444-34-0,34175-50-3,34175-53-6,37133-75-8,54984-01-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate; C₆₅H₈₃N₆O₄⁽¹⁺⁾*I^(1-); potassium osmate(VI) dihydrate; potassium hexacyanoferrate(III); methanesulfonamide / tert-butyl alcohol; water / 30 h / 0 °C / Inert atmosphere

2.1: methanesulfonyl chloride; pyridine / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

With pyridine; potassium osmate(VI) dihydrate; methanesulfonamide; C₆₅H₈₃N₆O₄⁽¹⁺⁾*I^(1-); potassium carbonate; methanesulfonyl chloride; potassium hexacyanoferrate(III); In dichloromethane; water; tert-butyl alcohol; 1.1: |Sharpless Dihydroxylation;

DOI:10.1002/anie.202104014

upstream raw materials:

farnesol

farnesyl acetate