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

Base Information

Chemical Name:[(2R,4R,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(4-butyl-phenoxy)-hexyl]-4-(dimethyl-phenyl-silanyl)-tetrahydro-furan-2-yl]-methanol
CAS No.:926030-14-0
Molecular Formula:C₃₅H₅₈O₄Si₂
Molecular Weight:599.014
Hs Code.:

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

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Chemical Property of [(2R,4R,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(4-butyl-phenoxy)-hexyl]-4-(dimethyl-phenyl-silanyl)-tetrahydro-furan-2-yl]-methanol

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Technology Process of [(2R,4R,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(4-butyl-phenoxy)-hexyl]-4-(dimethyl-phenyl-silanyl)-tetrahydro-furan-2-yl]-methanol

There total 8 articles about [(2R,4R,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(4-butyl-phenoxy)-hexyl]-4-(dimethyl-phenyl-silanyl)-tetrahydro-furan-2-yl]-methanol 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: 92.0%

: 926030-13-9
(2S,3R,5R)-5-benzyloxymethyl-2-[(1R)-1-(tert-butyldimethylsilyloxy)-6-(4-butylphenyloxy)hexyl]-3-(dimethylphenylsilyl)tetrahydrofuran

: 926030-14-0
[(2R,4R,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(4-butyl-phenoxy)-hexyl]-4-(dimethyl-phenyl-silanyl)-tetrahydro-furan-2-yl]-methanol

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

: 926030-14-0
[(2R,4R,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(4-butyl-phenoxy)-hexyl]-4-(dimethyl-phenyl-silanyl)-tetrahydro-furan-2-yl]-methanol

Guidance literature:: Multi-step reaction with 4 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: 81 percent / SnCl₄; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 h / -45 °C

4.1: 92 percent / hydrogen / Pd(OH)2 on carbon / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; n-butyllithium; 4 A molecular sieve; potassium tert-butylate; hydrogen; tin(IV) chloride; 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

: 926030-14-0
[(2R,4R,5S)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-(4-butyl-phenoxy)-hexyl]-4-(dimethyl-phenyl-silanyl)-tetrahydro-furan-2-yl]-methanol

Guidance literature:: Multi-step reaction with 5 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: 81 percent / SnCl₄; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 h / -45 °C

5.1: 92 percent / hydrogen / Pd(OH)2 on carbon / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; potassium tert-butylate; hydrogen; tin(IV) chloride; 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