Acetic acid (R)-6-(4-butyl-phenoxy)-1-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexyl ester

Base Information

Chemical Name:Acetic acid (R)-6-(4-butyl-phenoxy)-1-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexyl ester
CAS No.:954370-67-3
Molecular Formula:C₂₃H₃₆O₅
Molecular Weight:392.536
Hs Code.:

Synonyms:Acetic acid (R)-6-(4-butyl-phenoxy)-1-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexyl ester

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Chemical Property of Acetic acid (R)-6-(4-butyl-phenoxy)-1-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexyl ester

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Technology Process of Acetic acid (R)-6-(4-butyl-phenoxy)-1-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexyl ester

There total 10 articles about Acetic acid (R)-6-(4-butyl-phenoxy)-1-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexyl ester 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:

: 926030-07-1
(2R,5S)-2-[(1R)-1-acetyloxy-6-(4-butylphenyloxy)hexyl]-5-benzyloxymethyl-tetrahydrofuran

: 954370-67-3
Acetic acid (R)-6-(4-butyl-phenoxy)-1-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexyl ester

Guidance literature:: With hydrogen; palladium hydroxide - carbon; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1016/j.tet.2006.11.057

Reference yield:

: 926029-92-7
6-(4-butylphenyloxy)-1-hexanal

: 954370-67-3
Acetic acid (R)-6-(4-butyl-phenoxy)-1-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - -45 °C

1.2: 51 percent / (-)-Ipc₂BOMe; BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

2.1: 98 percent / imidazole / dimethylformamide / 48 h / 50 °C

3.1: 56 percent / BF₃*Et₂O; molecular sieves 4 Angstroem / CH₂Cl₂ / 22 h / -78 - -45 °C

4.1: 96 percent / TBAF / dimethylformamide; tetrahydrofuran / 5.5 h / 90 °C

5.1: 92 percent / DMAP / CH₂Cl₂ / 1 h / 0 - 35 °C

6.1: hydrogen / Pd(OH)2 on carbon / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; dmap; n-butyllithium; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; palladium hydroxide - carbon; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2006.11.057

Reference yield:

: 117947-71-4
6-(4-butyl-phenoxy)-hexan-1-ol

: 954370-67-3
Acetic acid (R)-6-(4-butyl-phenoxy)-1-((2R,5S)-5-hydroxymethyl-tetrahydro-furan-2-yl)-hexyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 84 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1 h / -78 - 0 °C

2.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 - -45 °C

2.2: 51 percent / (-)-Ipc₂BOMe; BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

3.1: 98 percent / imidazole / dimethylformamide / 48 h / 50 °C

4.1: 56 percent / BF₃*Et₂O; molecular sieves 4 Angstroem / CH₂Cl₂ / 22 h / -78 - -45 °C

5.1: 96 percent / TBAF / dimethylformamide; tetrahydrofuran / 5.5 h / 90 °C

6.1: 92 percent / DMAP / CH₂Cl₂ / 1 h / 0 - 35 °C

7.1: hydrogen / Pd(OH)2 on carbon / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; dmap; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; palladium hydroxide - carbon; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation;
DOI:10.1016/j.tet.2006.11.057