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

Base Information

Chemical Name:(2S,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilyloxy)-6-(4-butylphenyloxy)hexyl]-4-(dimethylphenylsilyl)tetrahydrofuran-2-carbaldehyde
CAS No.:926030-03-7
Molecular Formula:C₃₅H₅₆O₄Si₂
Molecular Weight:596.998
Hs Code.:

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

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Chemical Property of (2S,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilyloxy)-6-(4-butylphenyloxy)hexyl]-4-(dimethylphenylsilyl)tetrahydrofuran-2-carbaldehyde

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Technology Process of (2S,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilyloxy)-6-(4-butylphenyloxy)hexyl]-4-(dimethylphenylsilyl)tetrahydrofuran-2-carbaldehyde

There total 9 articles about (2S,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilyloxy)-6-(4-butylphenyloxy)hexyl]-4-(dimethylphenylsilyl)tetrahydrofuran-2-carbaldehyde 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:

: [5-[1-(tert-butyl-dimethyl-silanyloxy)-6-(4-butyl-phenoxy)-hexyl]-4-(dimethyl-phenyl-silanyl)-tetrahydro-furan-2-yl]-methanol

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

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 0 ℃; for 1h;
DOI:10.1016/j.tet.2006.11.057

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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: 113 mg / hydrogen / Pd(OH)2 on carbon / tetrahydrofuran / 2 h / 20 °C

5.1: 85 mg / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1 h / -78 - 0 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; dimethyl sulfoxide; triethylamine; palladium hydroxide - carbon; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 5.1: Swern oxidation;
DOI:10.1016/j.tet.2006.11.057

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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: 113 mg / hydrogen / Pd(OH)2 on carbon / tetrahydrofuran / 2 h / 20 °C

6.1: 85 mg / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1 h / -78 - 0 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; dimethyl sulfoxide; triethylamine; palladium hydroxide - carbon; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation / 6.1: Swern oxidation;
DOI:10.1016/j.tet.2006.11.057