(S)-(E)-4-(2-(methoxymethoxy)-3-(4-(methoxymethoxy)butyl)phenyl)but-3-en-2-ol

Base Information

• Chemical Name: (S)-(E)-4-(2-(methoxymethoxy)-3-(4-(methoxymethoxy)butyl)phenyl)but-3-en-2-ol
• CAS No.: 1352145-59-5
• Molecular Formula: C₁₈H₂₈O₅
• Molecular Weight: 324.417
• Mol file: 1352145-59-5.mol

Synonyms:(S)-(E)-4-(2-(methoxymethoxy)-3-(4-(methoxymethoxy)butyl)phenyl)but-3-en-2-ol

Chemical Property of (S)-(E)-4-(2-(methoxymethoxy)-3-(4-(methoxymethoxy)butyl)phenyl)but-3-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(E)-4-(2-(methoxymethoxy)-3-(4-(methoxymethoxy)butyl)phenyl)but-3-en-2-ol

There total 4 articles about (S)-(E)-4-(2-(methoxymethoxy)-3-(4-(methoxymethoxy)butyl)phenyl)but-3-en-2-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: 45.0%

vinyl acetate (108-05-4,9003-20-7) + (E)-4-(2-(methoxymethoxy)-3-(4-(methoxymethoxy)butyl)phenyl)but-3-en-2-ol (1352145-55-1) → (S)-(E)-4-(2-(methoxymethoxy)-3-(4-(methoxymethoxy)butyl)phenyl)but-3-en-2-ol (1352145-59-5) + (R)-(E)-4-(2-(methoxymethoxy)-3-(4-(methoxymethoxy)butyl)phenyl)but-3-en-2-ol (1352145-58-4) + C20H30O6 (1352145-57-3)

Guidance literature:

With Burkholderia cepacia lipase; In tert-butylmethyl ether; at 20 ℃; for 24h; optical yield given as %ee; Inert atmosphere; Resolution of racemate; Enzymatic reaction;

DOI:10.1021/ol203060v

Reference yield:

C18H26O5 (1352145-56-2) → (S)-(E)-4-(2-(methoxymethoxy)-3-(4-(methoxymethoxy)butyl)phenyl)but-3-en-2-ol (1352145-59-5) + C20H30O6 (1352145-57-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere

2: Burkholderia cepacia lipase / tert-butylmethyl ether / 24 h / 20 °C / Inert atmosphere; Resolution of racemate; Enzymatic reaction

With Burkholderia cepacia lipase; sodium tetrahydroborate; In methanol; tert-butylmethyl ether;

DOI:10.1021/ol203060v

Reference yield:

C14H22O4 (1352145-53-9) → (S)-(E)-4-(2-(methoxymethoxy)-3-(4-(methoxymethoxy)butyl)phenyl)but-3-en-2-ol (1352145-59-5) + C20H30O6 (1352145-57-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tert.-butyl lithium / hexane; pentane / 2 h / 0 °C / Inert atmosphere

1.2: 12 h / 20 °C / Inert atmosphere

2.1: sodium hydroxide / water / 6 h / 0 - 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate / methanol / 1 h / 0 °C / Inert atmosphere

4.1: Burkholderia cepacia lipase / tert-butylmethyl ether / 24 h / 20 °C / Inert atmosphere; Resolution of racemate; Enzymatic reaction

With Burkholderia cepacia lipase; sodium tetrahydroborate; tert.-butyl lithium; sodium hydroxide; In methanol; hexane; tert-butylmethyl ether; water; pentane; 2.1: Aldol condensation;

DOI:10.1021/ol203060v

upstream raw materials:

vinyl acetate

(E)-4-(2-(methoxymethoxy)-3-(4-(methoxymethoxy)butyl)phenyl)but-3-en-2-ol

C₁₈H₂₆O₅

C₁₄H₂₂O₄