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

Base Information

• Chemical Name: (1'R,3S,5S)-2-allyl-6-hydroxybenzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester
• CAS No.: 335163-27-4
• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.381
• Mol file: 335163-27-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (1'R,3S,5S)-2-allyl-6-hydroxybenzoic 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:

(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 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester (335163-27-4)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With triphenylphosphine; silver carbonate; diethylazodicarboxylate; In tetrahydrofuran; benzene; 2: Mitsunobu reaction;

DOI:10.1021/jo0301550

Reference yield:

2-allyl-6-methoxy-benzoic acid (325172-28-9) → (1'R,3S,5S)-2-allyl-6-hydroxybenzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester (335163-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / n-Bu₄NI; BCl₃ / CH₂Cl₂ / -78 - 20 °C

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

With boron trichloride; tetra-(n-butyl)ammonium iodide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 2: Mitsunobu reaction;

DOI:10.1021/jo0301550

Reference yield:

(S)-2,2-Dimethyl-5-((R)-1-methyl-but-3-enyl)-tetrahydro-furo[2,3-d][1,3]dioxole → (1'R,3S,5S)-2-allyl-6-hydroxybenzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester (335163-27-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / aq. acetic acid / 6 h / 70 °C

2: 85 percent / Ag₂CO₃-Celite / 1 h / 80 °C

3: 85 percent / Ph₃P; DEAD / tetrahydrofuran / 1 h / -20 - 0 °C

With acetic acid; triphenylphosphine; silver carbonate; diethylazodicarboxylate; In tetrahydrofuran; 3: Mitsunobu esterification;

DOI:10.1039/b008842k

upstream raw materials:

(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

2-allyl-6-methoxy-benzoic acid

(1'R,2R,3R,5S)-2,2-dimethyl-5-(1'-methylbut-3'-enyl)tetrahydrofuro[2,3-d][1,3]dioxole

Downstream raw materials:

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

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

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