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

Base Information

• Chemical Name: (1'R,3S,5S)-2-allyl-6-hydroxybenzoic acid 2-hydroxy-5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester
• CAS No.: 335163-29-6
• Molecular Formula: C₁₉H₂₄O₅
• Molecular Weight: 332.397

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

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

Chemical Property:

Purity/Quality:

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

There total 10 articles about (1'R,3S,5S)-2-allyl-6-hydroxybenzoic acid 2-hydroxy-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: 82.0%

(1'R,3S,5S)-2-allyl-6-hydroxybenzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester (335163-27-4) → (1'R,3S,5S)-2-allyl-6-hydroxybenzoic acid 2-hydroxy-5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester (335163-29-6)

Guidance literature:

With diisobutylaluminium hydride; In diethyl ether; toluene; at -78 ℃; for 0.5h;

DOI:10.1021/jo0301550

Reference yield:

(1'R,3R,5S)-5-(1'-methylbut-3'-enyl)tetrahydrofuran-2,3-diol (335163-26-3) → (1'R,3S,5S)-2-allyl-6-hydroxybenzoic acid 2-hydroxy-5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester (335163-29-6)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 90 percent / diethyl azodicarboxylate; Ph₃P / tetrahydrofuran / -78 - 20 °C

3: 82 percent / DIBAL-H / diethyl ether; toluene / 0.5 h / -78 °C

With diisobutylaluminium hydride; triphenylphosphine; silver carbonate; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; toluene; benzene; 2: Mitsunobu reaction;

DOI:10.1021/jo0301550

Reference yield:

(1'R,3R,5S)-3-hydroxy-5-(1'-methylbut-3'-enyl)dihydrofuran-2-one (335163-22-9) → (1'R,3S,5S)-2-allyl-6-hydroxybenzoic acid 2-hydroxy-5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester (335163-29-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / diethyl azodicarboxylate; Ph₃P / tetrahydrofuran / -78 - 20 °C

2: 82 percent / DIBAL-H / diethyl ether; toluene / 0.5 h / -78 °C

With diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; toluene; 1: Mitsunobu reaction;

DOI:10.1021/jo0301550

upstream raw materials:

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

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

(1'R,3R,5S)-5-(1'-methylbut-3'-enyl)tetrahydrofuran-2,3-diol

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

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