(+)-(3R)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol

Base Information

• Chemical Name: (+)-(3R)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol
• CAS No.: 871809-93-7
• Molecular Formula: C₁₉H₂₂O₂
• Molecular Weight: 282.382
• Mol file: 871809-93-7.mol

Synonyms:(+)-(3R)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol

Chemical Property of (+)-(3R)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (+)-(3R)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol

There total 23 articles about (+)-(3R)-1-[4-(benzyloxy)phenyl]hex-5-en-3-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: 76.0%

allyltributylstanane (24850-33-7) + 3-(4-(benzyloxy)phenyl)propanal (68486-77-1) → (+)-(3R)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol (871809-93-7)

Guidance literature:

3-(4-(benzyloxy)phenyl)propanal; With titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; In dichloromethane; at 20 ℃; Molecular sieve; Inert atmosphere;

allyltributylstanane; In dichloromethane; at -78 - -25 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1002/hlca.201000096

Reference yield: 70.0%

3-(4-(benzyloxy)phenyl)propanal (68486-77-1) + allylmagnesium bromide (1730-25-2) → (+)-(3R)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol (871809-93-7)

Guidance literature:

allylmagnesium bromide; With C₅H₁₀*C₃₁H₂₈O₄^(2-)*Cl^(1-)*Ti⁽³⁺⁾; In diethyl ether; at 0 ℃; for 1.5h; Inert atmosphere;

3-(4-(benzyloxy)phenyl)propanal; In diethyl ether; at -78 ℃; for 5.5h; enantioselective reaction;

DOI:10.1039/c8ob02052c

Reference yield: 44.0%

1-(4-(benzyloxy)phenyl)hex-5-en-3-ol (850251-73-9) + vinyl acetate (108-05-4,9003-20-7) → (+)-(3R)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol (871809-93-7) + (S)-1-[4-(benzyloxy)phenyl]hex-5-en-3-yl acetate + (-)-(3S)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol (767330-04-1)

Guidance literature:

With Pseudomonas cepacia lipase; In di-isopropyl ether; at 30 ℃; for 24h; Solvent; Reagent/catalyst; enantioselective reaction; Catalytic behavior; Inert atmosphere; Enzymatic reaction;

DOI:10.14233/ajchem.2017.20816

upstream raw materials:

3-(4-(benzyloxy)phenyl)propanal

allylmagnesium bromide

(1R,2R)-2-exo-hydroxy-2-endo-allyl-1,7,7-trimethylbicyclo<2.2.1>heptane

(+)-diisopinocampheylallylborane

Downstream raw materials:

(+)-(5E)-4'-O-benzyl-5,6-didehydro-4''-O-methylcentrolobol

(3R)-1-[4-(benzyloxy)phenyl]hex-5-en-3-yl (2S)-3,3,3-trifluoro-2-methoxy-2-phenylpropionate

(-)-(3S)-1-[4-(benzyloxy)phenyl]hex-5-en-3-ol

(S)-1-[4-(benzyloxy)phenyl]hex-5-en-3-yl acrylate