(1'R,3S,5S)-2-allyl-6-methoxybenzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester

Base Information

Chemical Name:(1'R,3S,5S)-2-allyl-6-methoxybenzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester
CAS No.:642486-88-2
Molecular Formula:C₂₀H₂₄O₅
Molecular Weight:344.408
Hs Code.:

Synonyms:(1'R,3S,5S)-2-allyl-6-methoxybenzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester

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Chemical Property of (1'R,3S,5S)-2-allyl-6-methoxybenzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester

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Technology Process of (1'R,3S,5S)-2-allyl-6-methoxybenzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester

There total 6 articles about (1'R,3S,5S)-2-allyl-6-methoxybenzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl 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: 98.0%

: 335163-22-9
(1'R,3R,5S)-3-hydroxy-5-(1'-methylbut-3'-enyl)dihydrofuran-2-one

: 325172-28-9
2-allyl-6-methoxy-benzoic acid

: 642486-88-2
(1'R,3S,5S)-2-allyl-6-methoxybenzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 5h;
DOI:10.1021/jo0301550

Reference yield:

: 58475-17-5
(R)-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol

: 642486-88-2
(1'R,3S,5S)-2-allyl-6-methoxybenzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

2.1: CuCN; MeLi / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

2.2: 375 mg / tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

3.1: 83 percent / aq. AcOH / 5 h / 50 °C

4.1: 95 percent / Ag₂CO₃*celite / benzene / 1 h / Heating

5.1: 98 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 5 h / 20 °C

With 2,6-dimethylpyridine; methyllithium; acetic acid; triphenylphosphine; silver carbonate; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; benzene; 5.1: Mitsunobu reaction;
DOI:10.1021/jo0301550

Reference yield:

: 579-75-9
2-Methoxybenzoic acid

: 642486-88-2
(1'R,3S,5S)-2-allyl-6-methoxybenzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: TMEDA; sec-BuLi; cyclohexane / tetrahydrofuran / 1.5 h / -90 - -78 °C

1.2: 46 percent / tetrahydrofuran / 1.5 h / -78 °C

2.1: 98 percent / Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 5 h / 20 °C

With N,N,N,N,-tetramethylethylenediamine; cyclohexane; sec.-butyllithium; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 2.1: Mitsunobu reaction;
DOI:10.1021/jo0301550