(2E,4E,6S,7S)-7,8-O-isopropylidene-6-(4-nitrobenzoyloxy)-7,8-dihydroxy-2,4-octadien-1-yl methyl maleate

Base Information

Chemical Name:(2E,4E,6S,7S)-7,8-O-isopropylidene-6-(4-nitrobenzoyloxy)-7,8-dihydroxy-2,4-octadien-1-yl methyl maleate
CAS No.:853953-41-0
Molecular Formula:C₂₃H₂₅NO₁₀
Molecular Weight:475.452
Hs Code.:

Synonyms:(2E,4E,6S,7S)-7,8-O-isopropylidene-6-(4-nitrobenzoyloxy)-7,8-dihydroxy-2,4-octadien-1-yl methyl maleate

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Chemical Property of (2E,4E,6S,7S)-7,8-O-isopropylidene-6-(4-nitrobenzoyloxy)-7,8-dihydroxy-2,4-octadien-1-yl methyl maleate

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Technology Process of (2E,4E,6S,7S)-7,8-O-isopropylidene-6-(4-nitrobenzoyloxy)-7,8-dihydroxy-2,4-octadien-1-yl methyl maleate

There total 9 articles about (2E,4E,6S,7S)-7,8-O-isopropylidene-6-(4-nitrobenzoyloxy)-7,8-dihydroxy-2,4-octadien-1-yl methyl maleate 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: 82.0%

: 122-04-3
4-nitro-benzoyl chloride

: 192331-13-8
(2E,4E,6S,7S)-7,8-O-isopropylidene-6,7,8-trihydroxy-2,4-octadien-1-yl methyl maleate

: 853953-41-0
(2E,4E,6S,7S)-7,8-O-isopropylidene-6-(4-nitrobenzoyloxy)-7,8-dihydroxy-2,4-octadien-1-yl methyl maleate

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 18h;
DOI:10.1002/chem.200401215

Reference yield:

: 114185-07-8
ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate

: 853953-41-0
(2E,4E,6S,7S)-7,8-O-isopropylidene-6-(4-nitrobenzoyloxy)-7,8-dihydroxy-2,4-octadien-1-yl methyl maleate

Guidance literature:: Multi-step reaction with 8 steps

1.1: 68 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

2.1: 86 percent / DIBALH / CH₂Cl₂; toluene / -100 °C

3.1: CH₂Cl₂ / 1.5 h / Heating

3.2: thiophenol; AIBN / benzene / 3 h / Heating; UV irradiation

4.1: 3.50 g / DIBALH / CH₂Cl₂; toluene / -78 °C

5.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0.17 h / 20 °C

6.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 20 °C

7.1: 74 percent / diethyl ether / 0 °C

8.1: 82 percent / pyridine; DMAP / CH₂Cl₂ / 18 h / 20 °C

With pyridine; 1H-imidazole; dmap; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Wittig reaction;
DOI:10.1002/chem.200401215

Reference yield:

: 879572-95-9
ethyl (2R,3S)-3,4-O-isopropylidene-2-[(tert-butyldimethylsilyl)oxy]-3,4-dihydroxybutanoate

: 853953-41-0
(2E,4E,6S,7S)-7,8-O-isopropylidene-6-(4-nitrobenzoyloxy)-7,8-dihydroxy-2,4-octadien-1-yl methyl maleate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 86 percent / DIBALH / CH₂Cl₂; toluene / -100 °C

2.1: CH₂Cl₂ / 1.5 h / Heating

2.2: thiophenol; AIBN / benzene / 3 h / Heating; UV irradiation

3.1: 3.50 g / DIBALH / CH₂Cl₂; toluene / -78 °C

4.1: 99 percent / Et₃N; DMAP / CH₂Cl₂ / 0.17 h / 20 °C

5.1: 85 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 20 °C

6.1: 74 percent / diethyl ether / 0 °C

7.1: 82 percent / pyridine; DMAP / CH₂Cl₂ / 18 h / 20 °C

With pyridine; dmap; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 2.1: Wittig reaction;
DOI:10.1002/chem.200401215