(2R,3R)-3-[3-[(E)-but-2-enyloxy]-5-methyl-4-(pivaloyloxy)phenyl]-2-methylpent-4-enoic acid

Base Information

Chemical Name:(2R,3R)-3-[3-[(E)-but-2-enyloxy]-5-methyl-4-(pivaloyloxy)phenyl]-2-methylpent-4-enoic acid
CAS No.:1414861-36-1
Molecular Formula:C₂₂H₃₀O₅
Molecular Weight:374.477
Hs Code.:

Synonyms:(2R,3R)-3-[3-[(E)-but-2-enyloxy]-5-methyl-4-(pivaloyloxy)phenyl]-2-methylpent-4-enoic acid

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Chemical Property of (2R,3R)-3-[3-[(E)-but-2-enyloxy]-5-methyl-4-(pivaloyloxy)phenyl]-2-methylpent-4-enoic acid

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Technology Process of (2R,3R)-3-[3-[(E)-but-2-enyloxy]-5-methyl-4-(pivaloyloxy)phenyl]-2-methylpent-4-enoic acid

There total 9 articles about (2R,3R)-3-[3-[(E)-but-2-enyloxy]-5-methyl-4-(pivaloyloxy)phenyl]-2-methylpent-4-enoic acid 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%

: 2408-20-0
prop-2-enyl propanoate

: 1414861-35-0
2-[(E)-but-2-en-1-yloxy]-6-methyl-4-[(E)-3-(propionyloxy)prop-1-en-1-yl]phenyl pivalate

: 1414861-36-1
(2R,3R)-3-[3-[(E)-but-2-enyloxy]-5-methyl-4-(pivaloyloxy)phenyl]-2-methylpent-4-enoic acid

Guidance literature:: prop-2-enyl propanoate; 2-[(E)-but-2-en-1-yloxy]-6-methyl-4-[(E)-3-(propionyloxy)prop-1-en-1-yl]phenyl pivalate; With (4S,5S)-1,3-bis[(3,5-bis(trifluoromethyl)phenyl)sulfonyl]-2-bromo-4,5-diphenyl-1,3,2-diazaborolidine; triethylamine; In toluene; at -78 - 20 ℃; for 22h; Inert atmosphere;

With hydrogenchloride; water; In toluene; at 20 ℃; for 0.5h; diastereoselective reaction; Inert atmosphere;
DOI:10.1055/s-0032-1316643

Reference yield:

: 1414861-31-6
5-iodo-2-(methoxymethoxy)-3-methylphenol

: 1414861-36-1
(2R,3R)-3-[3-[(E)-but-2-enyloxy]-5-methyl-4-(pivaloyloxy)phenyl]-2-methylpent-4-enoic acid

Guidance literature:: Multi-step reaction with 5 steps

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 19 h / 0 - 20 °C / Inert atmosphere

2.1: acetyl chloride / methanol; dichloromethane / 24 h / 20 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

4.1: potassium carbonate; palladium diacetate / benzene / 24 h / Inert atmosphere; Reflux

5.1: (4S,5S)-1,3-bis[(3,5-bis(trifluoromethyl)phenyl)sulfonyl]-2-bromo-4,5-diphenyl-1,3,2-diazaborolidine; triethylamine / toluene / 22 h / -78 - 20 °C / Inert atmosphere

5.2: 0.5 h / 20 °C / Inert atmosphere

With dmap; (4S,5S)-1,3-bis[(3,5-bis(trifluoromethyl)phenyl)sulfonyl]-2-bromo-4,5-diphenyl-1,3,2-diazaborolidine; di-isopropyl azodicarboxylate; potassium carbonate; palladium diacetate; triethylamine; acetyl chloride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene; 4.1: |Heck Reaction;
DOI:10.1055/s-0032-1316643

Reference yield:

: 1414861-32-7
(E)-1-(but-2-en-1-yloxy)-5-iodo-2-(methoxymethoxy)-3-methylbenzene

: 1414861-36-1
(2R,3R)-3-[3-[(E)-but-2-enyloxy]-5-methyl-4-(pivaloyloxy)phenyl]-2-methylpent-4-enoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: acetyl chloride / methanol; dichloromethane / 24 h / 20 °C / Inert atmosphere

2.1: dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

3.1: potassium carbonate; palladium diacetate / benzene / 24 h / Inert atmosphere; Reflux

4.1: (4S,5S)-1,3-bis[(3,5-bis(trifluoromethyl)phenyl)sulfonyl]-2-bromo-4,5-diphenyl-1,3,2-diazaborolidine; triethylamine / toluene / 22 h / -78 - 20 °C / Inert atmosphere

4.2: 0.5 h / 20 °C / Inert atmosphere

With dmap; (4S,5S)-1,3-bis[(3,5-bis(trifluoromethyl)phenyl)sulfonyl]-2-bromo-4,5-diphenyl-1,3,2-diazaborolidine; potassium carbonate; palladium diacetate; triethylamine; acetyl chloride; In methanol; dichloromethane; toluene; benzene; 3.1: |Heck Reaction;
DOI:10.1055/s-0032-1316643