(2E,4Z)-(S)-6-Benzyloxy-4-bromo-9-cyano-nona-2,4-dienoic acid methyl ester

Base Information

Chemical Name:(2E,4Z)-(S)-6-Benzyloxy-4-bromo-9-cyano-nona-2,4-dienoic acid methyl ester
CAS No.:132047-77-9
Molecular Formula:C₁₈H₂₀BrNO₃
Molecular Weight:378.266
Hs Code.:

Synonyms:(2E,4Z)-(S)-6-Benzyloxy-4-bromo-9-cyano-nona-2,4-dienoic acid methyl ester

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Chemical Property of (2E,4Z)-(S)-6-Benzyloxy-4-bromo-9-cyano-nona-2,4-dienoic acid methyl ester

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Technology Process of (2E,4Z)-(S)-6-Benzyloxy-4-bromo-9-cyano-nona-2,4-dienoic acid methyl ester

There total 10 articles about (2E,4Z)-(S)-6-Benzyloxy-4-bromo-9-cyano-nona-2,4-dienoic acid methyl ester 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: 96.0%

: 100843-81-0
(Z)-(S)-5-Benzyloxy-7-bromo-8-oxo-oct-6-enenitrile

: 21204-67-1,2605-67-6
methyl (triphenylphosphoranylidene)acetate

: 132047-77-9
(2E,4Z)-(S)-6-Benzyloxy-4-bromo-9-cyano-nona-2,4-dienoic acid methyl ester

Guidance literature:: In dichloromethane; at 23 ℃;
DOI:10.1021/jo00003a049

Reference yield:

: 79364-35-5
(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

: 132047-77-9
(2E,4Z)-(S)-6-Benzyloxy-4-bromo-9-cyano-nona-2,4-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1) NaH / 1) DMF, 0 deg C, 15 min, 2) 23 deg C, 2h

2: 1) 1M BH₃*THF, 2) 3M NaOH, 30percent H₂O₂ / 1) 23 deg C, 2h, 2) 23 deg C, 2.3h

3: NEt₃ / CH₂Cl₂ / 0.33 h / 0 °C

4: n-Bu₄NI / dimethylformamide / 2 h / 80 °C

5: 84 percent / 50percent HOAc / methanol / 8 h / Heating

6: 100 percent / NaIO₄ / tetrahydrofuran / 1 h / 23 °C

7: 83 percent / benzene / 3 h / Heating

8: 1) Br₂-dioxane, 2) pyridine / 1) CHCl₃, 0 deg C, 1h, 2a) 0 deg C, 30 min, 2b) 23 deg C, 2h

9: 96 percent / CH₂Cl₂ / 23 °C

With pyridine; sodium hydroxide; sodium periodate; borane-THF; dihydrogen peroxide; dioxane dibromide; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00003a049

Reference yield:

: 100-39-0
benzyl bromide

: 132047-77-9
(2E,4Z)-(S)-6-Benzyloxy-4-bromo-9-cyano-nona-2,4-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 1) NaH / 1) DMF, 0 deg C, 15 min, 2) 23 deg C, 2h

2: 1) 1M BH₃*THF, 2) 3M NaOH, 30percent H₂O₂ / 1) 23 deg C, 2h, 2) 23 deg C, 2.3h

3: NEt₃ / CH₂Cl₂ / 0.33 h / 0 °C

4: n-Bu₄NI / dimethylformamide / 2 h / 80 °C

5: 84 percent / 50percent HOAc / methanol / 8 h / Heating

6: 100 percent / NaIO₄ / tetrahydrofuran / 1 h / 23 °C

7: 83 percent / benzene / 3 h / Heating

8: 1) Br₂-dioxane, 2) pyridine / 1) CHCl₃, 0 deg C, 1h, 2a) 0 deg C, 30 min, 2b) 23 deg C, 2h

9: 96 percent / CH₂Cl₂ / 23 °C

With pyridine; sodium hydroxide; sodium periodate; borane-THF; dihydrogen peroxide; dioxane dibromide; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00003a049