(2R,3R,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-one

Base Information

• Chemical Name: (2R,3R,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-one
• CAS No.: 427875-98-7
• Molecular Formula: C₁₉H₂₈O₄
• Molecular Weight: 320.429
• Mol file: 427875-98-7.mol

Synonyms:(2R,3R,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-one

Chemical Property of (2R,3R,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-one

There total 1 articles about (2R,3R,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-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:

p-methoxybenzoylmethanol (4136-21-4) + trans-4-decenal (65405-70-1) → (2R,3R,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-one (427875-98-7) + (2R,3S,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-one (427875-99-8) + (2S,3R,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-one + (2S,3S,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-one

Guidance literature:

With LaLi₃ tris((S)-binaphthoxide); water; potassium hexamethylsilazane; In tetrahydrofuran; at -40 ℃; for 13h; Title compound not separated from byproducts.;

DOI:10.1021/jo0162538

Reference yield: 90.0%

bis(trichloromethyl) carbonate (32315-10-9) + (2R,3R,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-one (427875-98-7) → (2R,3R,6E)-2,3-carbonyldioxy-1-(4-methoxyphenyl)-6-dodecen-1-one (427876-11-7)

Guidance literature:

With pyridine; In dichloromethane; at -20 ℃; for 2h;

DOI:10.1021/jo0162538

Reference yield:

(2R,3R,6E)-2,3-dihydroxy-1-(4-methoxyphenyl)-6-dodecen-1-one (427875-98-7) → 4-methoxyphenyl (2R,3R,6E)-2,3-carbonyldioxy-6-dodecenoate

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / pyridine / CH₂Cl₂ / 2 h / -20 °C

2: 78 percent / trans-N,N-bis(p-toluenesulfonyl)-1,2-cyclohexanediamine; SnCl₄; bis(trimethylsilyl) peroxide / CH₂Cl₂ / 0.83 h / -20 °C

With pyridine; bis-trimethylsilanyl peroxide; trans-N,N-bis(p-toluenesulfonyl)-1,2-cyclohexanediamine; tin(IV) chloride; In dichloromethane; 2: Baeyer-Villiger oxidation;

DOI:10.1021/jo0162538

upstream raw materials:

p-methoxybenzoylmethanol

trans-4-decenal

Downstream raw materials:

(2R,3R,6E)-2,3-carbonyldioxy-1-(4-methoxyphenyl)-6-dodecen-1-one