methyl (2E,4E,6R,7S)-7-(3-acetamido-2,5-dihydroxyphenyl)-7-hydroxy-4,6-dimethylhepta-2,4-dienoate

Base Information

Chemical Name:methyl (2E,4E,6R,7S)-7-(3-acetamido-2,5-dihydroxyphenyl)-7-hydroxy-4,6-dimethylhepta-2,4-dienoate
CAS No.:1262790-22-6
Molecular Formula:C₁₈H₂₃NO₆
Molecular Weight:349.384
Hs Code.:

Synonyms:methyl (2E,4E,6R,7S)-7-(3-acetamido-2,5-dihydroxyphenyl)-7-hydroxy-4,6-dimethylhepta-2,4-dienoate

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Chemical Property of methyl (2E,4E,6R,7S)-7-(3-acetamido-2,5-dihydroxyphenyl)-7-hydroxy-4,6-dimethylhepta-2,4-dienoate

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Technology Process of methyl (2E,4E,6R,7S)-7-(3-acetamido-2,5-dihydroxyphenyl)-7-hydroxy-4,6-dimethylhepta-2,4-dienoate

There total 7 articles about methyl (2E,4E,6R,7S)-7-(3-acetamido-2,5-dihydroxyphenyl)-7-hydroxy-4,6-dimethylhepta-2,4-dienoate 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: 55.0%

: 1259234-80-4
(2E,4E,6R,7S)-methyl 7-(3-acetamido-2,5-dimethoxyphenyl)-7-(methoxymethoxy)-4,6-dimethylhepta-2,4-dienoate

: 1262790-22-6
methyl (2E,4E,6R,7S)-7-(3-acetamido-2,5-dihydroxyphenyl)-7-hydroxy-4,6-dimethylhepta-2,4-dienoate

Guidance literature:: With aluminum (III) chloride; In dichloromethane; 2-methylpropan-2-thiol; at 0 - 40 ℃; Inert atmosphere;
DOI:10.1021/ol102574d

Reference yield: 41.0%

: methyl (2E,4E,6R,7S)-7-(3-acetamido-2,5-dimethoxyphenyl)-7-(benzyloxy)-4,6-dimethylhepta-2,4-dienoate

: 1262790-22-6
methyl (2E,4E,6R,7S)-7-(3-acetamido-2,5-dihydroxyphenyl)-7-hydroxy-4,6-dimethylhepta-2,4-dienoate

Guidance literature:: With aluminum (III) chloride; 2-methylpropan-2-thiol; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;
DOI:10.1021/acs.orglett.6b02052

Reference yield:

: 74422-90-5
2,5-dimethoxy-3-nitrobenzaldehyde

: 1262790-22-6
methyl (2E,4E,6R,7S)-7-(3-acetamido-2,5-dihydroxyphenyl)-7-hydroxy-4,6-dimethylhepta-2,4-dienoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: trimethylsilyl trifluoromethanesulfonate / 24 h / -78 - -60 °C / Inert atmosphere

2.1: sulfur; sodium tetrahydroborate / tetrahydrofuran / 4 h / 70 °C / Inert atmosphere

3.1: triethylamine; dmap / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

4.1: cyclopentylmagnesium chloride; C₉H₂₅ClO₃Ti / diethyl ether; hexane; toluene / 5.83 h / -78 - -40 °C / Inert atmosphere

4.2: 4 h / -78 - 20 °C

5.1: 2-methylpropan-2-thiol; aluminum (III) chloride / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With dmap; aluminum (III) chloride; sodium tetrahydroborate; trimethylsilyl trifluoromethanesulfonate; C₉H₂₅ClO₃Ti; cyclopentylmagnesium chloride; sulfur; 2-methylpropan-2-thiol; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene;
DOI:10.1021/acs.orglett.6b02052