(-)-(1S)-4-((4R,E)-5-(tert-butyldiphenylsiloxy)-4-methyl-2-pentenyloxy)-1,5-dimethyl-9-oxo-8-oxabicyclo[4.3.0]nona-4,6-diene

Base Information

Chemical Name:(-)-(1S)-4-((4R,E)-5-(tert-butyldiphenylsiloxy)-4-methyl-2-pentenyloxy)-1,5-dimethyl-9-oxo-8-oxabicyclo[4.3.0]nona-4,6-diene
CAS No.:161807-14-3
Molecular Formula:C₃₂H₄₀O₄Si
Molecular Weight:516.753
Hs Code.:

Synonyms:(-)-(1S)-4-((4R,E)-5-(tert-butyldiphenylsiloxy)-4-methyl-2-pentenyloxy)-1,5-dimethyl-9-oxo-8-oxabicyclo[4.3.0]nona-4,6-diene

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Chemical Property of (-)-(1S)-4-((4R,E)-5-(tert-butyldiphenylsiloxy)-4-methyl-2-pentenyloxy)-1,5-dimethyl-9-oxo-8-oxabicyclo[4.3.0]nona-4,6-diene

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Technology Process of (-)-(1S)-4-((4R,E)-5-(tert-butyldiphenylsiloxy)-4-methyl-2-pentenyloxy)-1,5-dimethyl-9-oxo-8-oxabicyclo[4.3.0]nona-4,6-diene

There total 17 articles about (-)-(1S)-4-((4R,E)-5-(tert-butyldiphenylsiloxy)-4-methyl-2-pentenyloxy)-1,5-dimethyl-9-oxo-8-oxabicyclo[4.3.0]nona-4,6-diene 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: 77.0%

: (R)-(E)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-pentenyltrifluoromethane sulfonate

: 161023-28-5
(S)-(+)-4,7a-dimethyl-7,7a-dihydro-2-benzofuran-1,5(3H,6H)-dione

: 161807-14-3
(-)-(1S)-4-((4R,E)-5-(tert-butyldiphenylsiloxy)-4-methyl-2-pentenyloxy)-1,5-dimethyl-9-oxo-8-oxabicyclo[4.3.0]nona-4,6-diene

Guidance literature:: (S)-(+)-4,7a-dimethyl-7,7a-dihydro-2-benzofuran-1,5(3H,6H)-dione; With sodium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 1h; Inert atmosphere;

(R)-(E)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-pentenyltrifluoromethane sulfonate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -78 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.067

Reference yield:

: 917871-11-5
(R)-(E)-(+)-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-penten-1-ol

: 161807-14-3
(-)-(1S)-4-((4R,E)-5-(tert-butyldiphenylsiloxy)-4-methyl-2-pentenyloxy)-1,5-dimethyl-9-oxo-8-oxabicyclo[4.3.0]nona-4,6-diene

Guidance literature:: Multi-step reaction with 2 steps

1: nBuLi / -78 °C

2: NaHMDS / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 °C

With n-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;
DOI:10.1016/0040-4039(94)02390-W

Reference yield:

: 917871-10-4
(R)-(E)-(+)-ethyl-5-(tert-butyldiphenylsilyloxy)-4-methyl-2-pentenoate

: 161807-14-3
(-)-(1S)-4-((4R,E)-5-(tert-butyldiphenylsiloxy)-4-methyl-2-pentenyloxy)-1,5-dimethyl-9-oxo-8-oxabicyclo[4.3.0]nona-4,6-diene

Guidance literature:: Multi-step reaction with 3 steps

1.1: diisobutylaluminium hydride / diethyl ether; hexane / 5 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - 20 °C / Inert atmosphere

2.1: tert.-butyl lithium / diethyl ether; hexane / 0.17 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C / Inert atmosphere

3.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 1 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

With tert.-butyl lithium; sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane;
DOI:10.1016/j.tet.2011.09.067