(4Z,6E)-(2S,3S)-3-Hydroxy-2,4,6-trimethyl-7-(4-nitro-phenyl)-hepta-4,6-dienoic acid methoxy-methyl-amide

Base Information

Chemical Name:(4Z,6E)-(2S,3S)-3-Hydroxy-2,4,6-trimethyl-7-(4-nitro-phenyl)-hepta-4,6-dienoic acid methoxy-methyl-amide
CAS No.:444759-98-2
Molecular Formula:C₁₈H₂₄N₂O₅
Molecular Weight:348.399
Hs Code.:

Synonyms:(4Z,6E)-(2S,3S)-3-Hydroxy-2,4,6-trimethyl-7-(4-nitro-phenyl)-hepta-4,6-dienoic acid methoxy-methyl-amide

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Chemical Property of (4Z,6E)-(2S,3S)-3-Hydroxy-2,4,6-trimethyl-7-(4-nitro-phenyl)-hepta-4,6-dienoic acid methoxy-methyl-amide

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Technology Process of (4Z,6E)-(2S,3S)-3-Hydroxy-2,4,6-trimethyl-7-(4-nitro-phenyl)-hepta-4,6-dienoic acid methoxy-methyl-amide

There total 5 articles about (4Z,6E)-(2S,3S)-3-Hydroxy-2,4,6-trimethyl-7-(4-nitro-phenyl)-hepta-4,6-dienoic acid methoxy-methyl-amide 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: 78.0%

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: (S)-4-Benzyl-3-[(4Z,6E)-(2S,3S)-3-hydroxy-2,4,6-trimethyl-7-(4-nitro-phenyl)-hepta-4,6-dienoyl]-oxazolidin-2-one

: 444759-98-2
(4Z,6E)-(2S,3S)-3-Hydroxy-2,4,6-trimethyl-7-(4-nitro-phenyl)-hepta-4,6-dienoic acid methoxy-methyl-amide

Guidance literature:: With trimethylaluminum; In toluene; at 20 ℃;
DOI:10.1021/ol026069o

Reference yield:

: 58550-34-8,37524-18-8
(E)-2-methyl-3-(4-nitrophenyl)acrylaldehyde

: 444759-98-2
(4Z,6E)-(2S,3S)-3-Hydroxy-2,4,6-trimethyl-7-(4-nitro-phenyl)-hepta-4,6-dienoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / KHMDS; 18-crown-6 / tetrahydrofuran / -78 °C

2: 89 percent / DIBAH / CH₂Cl₂ / -78 °C

3: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

4: Bu₂BOTf; triethylamine / tetrahydrofuran / -78 - 0 °C

5: 78 percent / AlMe₃ / toluene / 20 °C

With 18-crown-6 ether; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; In tetrahydrofuran; dichloromethane; toluene; 1: Still-Gennari reaction / 3: Dess-Martin oxidation;
DOI:10.1021/ol026069o

Reference yield:

: 639008-87-0
2,4-dimethyl-5-(4-nitro-phenyl)-penta-(Z)-2,(E)-4-dienal

: 444759-98-2
(4Z,6E)-(2S,3S)-3-Hydroxy-2,4,6-trimethyl-7-(4-nitro-phenyl)-hepta-4,6-dienoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 2 steps

1: Bu₂BOTf; triethylamine / tetrahydrofuran / -78 - 0 °C

2: 78 percent / AlMe₃ / toluene / 20 °C

With di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; triethylamine; In tetrahydrofuran; toluene;
DOI:10.1021/ol026069o