(4E,6Z,2S,3R)-7-bromo-3-(tert-butyldiphenylsilyl)oxy-1,2-epoxy-2-methylhepta-4,6-diene

Base Information

Chemical Name:(4E,6Z,2S,3R)-7-bromo-3-(tert-butyldiphenylsilyl)oxy-1,2-epoxy-2-methylhepta-4,6-diene
CAS No.:439808-09-0
Molecular Formula:C₂₄H₂₉BrO₂Si
Molecular Weight:457.483
Hs Code.:

Synonyms:(4E,6Z,2S,3R)-7-bromo-3-(tert-butyldiphenylsilyl)oxy-1,2-epoxy-2-methylhepta-4,6-diene

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Chemical Property of (4E,6Z,2S,3R)-7-bromo-3-(tert-butyldiphenylsilyl)oxy-1,2-epoxy-2-methylhepta-4,6-diene

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Technology Process of (4E,6Z,2S,3R)-7-bromo-3-(tert-butyldiphenylsilyl)oxy-1,2-epoxy-2-methylhepta-4,6-diene

There total 3 articles about (4E,6Z,2S,3R)-7-bromo-3-(tert-butyldiphenylsilyl)oxy-1,2-epoxy-2-methylhepta-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: 89.0%

: 439808-08-9
(4E,2S,3R)-7,7-dibromo-3-(tert-butyldiphenylsilyl)oxy-1,2-epoxy-2-methylhepta-4,6-diene

: 439808-09-0
(4E,6Z,2S,3R)-7-bromo-3-(tert-butyldiphenylsilyl)oxy-1,2-epoxy-2-methylhepta-4,6-diene

Guidance literature:: With tri-n-butyl-tin hydride; triphenylphosphine; palladium diacetate; In benzene; at 20 ℃; for 2h;
DOI:10.1016/S0040-4020(02)00117-5

Reference yield:

: 356787-10-5
(2R,3S)-2-(tert-butyldiphenylsilyl)oxy-3,4-epoxy-3-methylbutanal

: 439808-09-0
(4E,6Z,2S,3R)-7-bromo-3-(tert-butyldiphenylsilyl)oxy-1,2-epoxy-2-methylhepta-4,6-diene

Guidance literature:: Multi-step reaction with 3 steps

1.1: LiCl; N,N-diisopropylethylamine / acetonitrile / 0.5 h / 20 °C

1.2: 54 percent / acetonitrile / 20 °C

2.1: 92 percent / CH₂Cl₂ / 1 h / -20 °C

3.1: 89 percent / triphenylphosphine; tributyltin hydride / palladium acetate / benzene / 2 h / 20 °C

With tri-n-butyl-tin hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; palladium diacetate; In dichloromethane; acetonitrile; benzene; 1.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/S0040-4020(02)00117-5

Reference yield:

: 439808-07-8
(2E,4R,5S)-4-(tert-butyldiphenylsilyl)oxy-5,6-epoxy-5-methylhex-2-enal

: 439808-09-0
(4E,6Z,2S,3R)-7-bromo-3-(tert-butyldiphenylsilyl)oxy-1,2-epoxy-2-methylhepta-4,6-diene

Guidance literature:: Multi-step reaction with 2 steps

1: 92 percent / CH₂Cl₂ / 1 h / -20 °C

2: 89 percent / triphenylphosphine; tributyltin hydride / palladium acetate / benzene / 2 h / 20 °C

With tri-n-butyl-tin hydride; triphenylphosphine; palladium diacetate; In dichloromethane; benzene;
DOI:10.1016/S0040-4020(02)00117-5