(5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one

Base Information

Chemical Name:(5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one
CAS No.:470470-80-5
Molecular Formula:C₄₀H₆₀O₅Si₂
Molecular Weight:677.084
Hs Code.:

Synonyms:(5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one

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Chemical Property of (5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one

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Technology Process of (5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one

There total 5 articles about (5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one 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: 76.0%

: 97250-25-4
tert-Butyldiphenylsilyl β-hydroxybutanone

: 470470-64-5
(S)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentanal

: 470470-80-5
(5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one

Guidance literature:: tert-Butyldiphenylsilyl β-hydroxybutanone; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

(S)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentanal; In tetrahydrofuran; hexane; at -78 ℃; for 0.0333333h; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.064

Reference yield:

: 147252-93-5
(3S)-3-(benzyloxy)-2,2-dimethyl-4-penten-1-ol

: 470470-80-5
(5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole; dmap; tetra-(n-butyl)ammonium iodide / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: borane / tetrahydrofuran / -18 - 20 °C / Inert atmosphere

2.2: 3 h / 50 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

4.2: 0.03 h / -78 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; oxalyl dichloride; borane; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 4.2: Aldol condensation;
DOI:10.1016/j.tet.2011.09.064

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 470470-80-5
(5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole; dmap; tetra-(n-butyl)ammonium iodide / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: borane / tetrahydrofuran / -18 - 20 °C / Inert atmosphere

2.2: 3 h / 50 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.33 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

4.2: 0.03 h / -78 °C / Inert atmosphere

With 1H-imidazole; dmap; n-butyllithium; oxalyl dichloride; borane; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 4.2: Aldol condensation;
DOI:10.1016/j.tet.2011.09.064