(2Z)-(4S)-4-benzyloxy-2-[(E)-5-bromo-4-methylpent-3-enyl]octa-2,7-dienenitrile

Base Information

Chemical Name:(2Z)-(4S)-4-benzyloxy-2-[(E)-5-bromo-4-methylpent-3-enyl]octa-2,7-dienenitrile
CAS No.:1609534-00-0
Molecular Formula:C₂₁H₂₆BrNO
Molecular Weight:388.348
Hs Code.:

Synonyms:(2Z)-(4S)-4-benzyloxy-2-[(E)-5-bromo-4-methylpent-3-enyl]octa-2,7-dienenitrile

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Chemical Property of (2Z)-(4S)-4-benzyloxy-2-[(E)-5-bromo-4-methylpent-3-enyl]octa-2,7-dienenitrile

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Technology Process of (2Z)-(4S)-4-benzyloxy-2-[(E)-5-bromo-4-methylpent-3-enyl]octa-2,7-dienenitrile

There total 5 articles about (2Z)-(4S)-4-benzyloxy-2-[(E)-5-bromo-4-methylpent-3-enyl]octa-2,7-dienenitrile 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: 91.0%

: 1609533-99-4
(2Z)-(4S)-4-benzyloxy-2-[(E)-5-hydroxy-4-methylpent-3-enyl]octa-2,7-dienenitrile

: 1609534-00-0
(2Z)-(4S)-4-benzyloxy-2-[(E)-5-bromo-4-methylpent-3-enyl]octa-2,7-dienenitrile

Guidance literature:: (2Z)-(4S)-4-benzyloxy-2-[(E)-5-hydroxy-4-methylpent-3-enyl]octa-2,7-dienenitrile; With triethylamine; Methanesulfonic anhydride; In dichloromethane; at 0 ℃; for 0.25h; Inert atmosphere;

With lithium bromide; In tetrahydrofuran; dichloromethane; at 20 ℃; for 3h; Inert atmosphere;
DOI:10.1016/j.tetlet.2014.04.018

Reference yield:

: 113730-85-1
(S)-1-((R)-1,4-dioxaspiro[4.5]decan-2-yl)pent-4-en-1-ol

: 1609534-00-0
(2Z)-(4S)-4-benzyloxy-2-[(E)-5-bromo-4-methylpent-3-enyl]octa-2,7-dienenitrile

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 12 h / 20 °C

2.1: hydrogenchloride / methanol; water / 15 h / 40 °C

3.1: sodium periodate / water; acetonitrile / 2 h / 0 °C

3.2: 0.17 h / -78 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / methanol / 13 h / 20 °C

5.1: triethylamine; Methanesulfonic anhydride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

5.2: 3 h / 20 °C / Inert atmosphere

With hydrogenchloride; sodium periodate; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; Methanesulfonic anhydride; In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1016/j.tetlet.2014.04.018

Reference yield:

: 1554519-04-8
(2R,3S)-3-(benzyloxy)hept-6-ene-1,2-diol

: 1609534-00-0
(2Z)-(4S)-4-benzyloxy-2-[(E)-5-bromo-4-methylpent-3-enyl]octa-2,7-dienenitrile

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium periodate / water; acetonitrile / 2 h / 0 °C

1.2: 0.17 h / -78 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / methanol / 13 h / 20 °C

3.1: triethylamine; Methanesulfonic anhydride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

3.2: 3 h / 20 °C / Inert atmosphere

With sodium periodate; pyridinium p-toluenesulfonate; triethylamine; Methanesulfonic anhydride; In methanol; dichloromethane; water; acetonitrile;
DOI:10.1016/j.tetlet.2014.04.018