(2R,2'S,5S,5'R)-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran

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Chemical Name:(2R,2'S,5S,5'R)-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran
CAS No.:926029-81-4
Molecular Formula:C₄₀H₆₂O₆
Molecular Weight:638.929
Hs Code.:

Synonyms:(2R,2'S,5S,5'R)-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran

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Chemical Property of (2R,2'S,5S,5'R)-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran

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Technology Process of (2R,2'S,5S,5'R)-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran

There total 10 articles about (2R,2'S,5S,5'R)-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran 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: 63.0%

: 926030-19-5
(3R,4S)-4-(tert-butyldimethylsilyloxy)-9-(4-butylphenyloxy)-3-(dimethylphenylsilyl)-1-nonene

: 926030-03-7
(2S,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilyloxy)-6-(4-butylphenyloxy)hexyl]-4-(dimethylphenylsilyl)tetrahydrofuran-2-carbaldehyde

: 926029-81-4
(2R,2'S,5S,5'R)-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran

Guidance literature:: (3R,4S)-4-(tert-butyldimethylsilyloxy)-9-(4-butylphenyloxy)-3-(dimethylphenylsilyl)-1-nonene; (2S,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilyloxy)-6-(4-butylphenyloxy)hexyl]-4-(dimethylphenylsilyl)tetrahydrofuran-2-carbaldehyde; With 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 1h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; N,N-dimethyl-formamide; at 90 ℃; for 6.5h;
DOI:10.1016/j.tet.2006.11.057

Reference yield:

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

: 926029-81-4
(2R,2'S,5S,5'R)-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 55 percent / (+)-Ipc₂BOMe; BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

2.1: 94 percent / imidazole / dimethylformamide / 48 h / 50 °C

3.1: BF₃*Et₂O; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / -78 °C

3.2: 63 percent / TBAF / dimethylformamide; tetrahydrofuran / 6.5 h / 90 °C

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

Reference yield:

: 926030-05-9
tert-butyl-[6-(4-butyl-phenoxy)-hexyloxy]-dimethyl-silane

: 926029-81-4
(2R,2'S,5S,5'R)-5-[(1S)-6-(4-butylphenyloxy)-1-hydroxyhexyl]-5'-[(1R)-6-(4-butylphenyloxy)-1-hydroxyhexyl]octahydro-2,2'-bifuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: TBAF / tetrahydrofuran / 3.5 h / 0 - 20 °C

2.1: 84 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1 h / -78 - 0 °C

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

3.2: 55 percent / (+)-Ipc₂BOMe; BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

4.1: 94 percent / imidazole / dimethylformamide / 48 h / 50 °C

5.1: BF₃*Et₂O; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / -78 °C

5.2: 63 percent / TBAF / dimethylformamide; tetrahydrofuran / 6.5 h / 90 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 2.1: Swern oxidation;
DOI:10.1016/j.tet.2006.11.057