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

Base Information

Chemical Name:(2S,3R,5R)-5-benzyloxymethyl-2-[(1R)-1-(tert-butyldimethylsilyloxy)-6-(4-butylphenyloxy)hexyl]-3-(dimethylphenylsilyl)tetrahydrofuran
CAS No.:926030-13-9
Molecular Formula:C₄₂H₆₄O₄Si₂
Molecular Weight:689.139
Hs Code.:

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

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Chemical Property of (2S,3R,5R)-5-benzyloxymethyl-2-[(1R)-1-(tert-butyldimethylsilyloxy)-6-(4-butylphenyloxy)hexyl]-3-(dimethylphenylsilyl)tetrahydrofuran

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Technology Process of (2S,3R,5R)-5-benzyloxymethyl-2-[(1R)-1-(tert-butyldimethylsilyloxy)-6-(4-butylphenyloxy)hexyl]-3-(dimethylphenylsilyl)tetrahydrofuran

There total 7 articles about (2S,3R,5R)-5-benzyloxymethyl-2-[(1R)-1-(tert-butyldimethylsilyloxy)-6-(4-butylphenyloxy)hexyl]-3-(dimethylphenylsilyl)tetrahydrofuran 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: 81.0%

: 926030-00-4
(3S,4R)-4-(tert-butyldimethylsilyloxy)-9-(4-butylphenyloxy)-3-(dimethylphenylsilyl)-1-nonene

: 60656-87-3
benzyloxyacetoaldehyde

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

Guidance literature:: With 4 A molecular sieve; tin(IV) chloride; In dichloromethane; at -45 ℃; for 20h;
DOI:10.1016/j.tet.2006.11.057

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

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

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

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; potassium tert-butylate; tin(IV) chloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Swern oxidation;
DOI:10.1016/j.tet.2006.11.057