(2R,3R,3aR,7aS)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ethanoate

Base Information

• Chemical Name: (2R,3R,3aR,7aS)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ethanoate
• CAS No.: 65409-11-2
• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.273
• Mol file: 65409-11-2.mol

Synonyms:(2R,3R,3aR,7aS)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ethanoate

Chemical Property of (2R,3R,3aR,7aS)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ethanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,3aR,7aS)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ethanoate

There total 14 articles about (2R,3R,3aR,7aS)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ethanoate 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: 96.0%

goniothalenol (65408-91-5) + acetic anhydride (108-24-7) → (2R,3R,3aR,7aS)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ethanoate (65409-11-2)

Guidance literature:

With pyridine; at 20 ℃; for 1h;

DOI:10.1021/np990089q

Reference yield: 93.0%

(5S,6R,7R,8S)-6-<8-acetoxy-7,8-dihydro-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one (153619-54-6) → (2R,3R,3aR,7aS)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ethanoate (65409-11-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(99)00023-X

Reference yield:

(S)-3-Hydroxy-3-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-propionic acid (124040-09-1) → Acetic acid (2S,3S)-5-oxo-2-phenyl-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-3-yl ester (65409-11-2,114488-18-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) dicyclohexylcarbodiimide / 2.) 4-dimethylaminopyridine / 1.) pyridine, RT, 6 h; 2.) RT, overnight

2: 87 percent / diazabicycloundecene / CH₂Cl₂ / 1 h / Ambient temperature

3: 47.7 percent / HF / 0.17 h / 0 °C

4: pyridine

With 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; dmap; hydrogen fluoride; In pyridine; dichloromethane;

DOI:10.1016/S0040-4020(01)80093-4

upstream raw materials:

(5S,6R,7R,8S)-6-<8-acetoxy-7,8-dihydro-7-(methoxymethoxy)styryl>-5-(methoxymethoxy)-5,6-dihydro-2H-pyran-2-one

goniothalenol

acetic anhydride

(-) Altholactone

Downstream raw materials:

goniothalenol

Acetic acid (2R,3R,3aR,6S,7R,7aS)-6,7-dihydroxy-5-oxo-2-phenyl-hexahydro-furo[3,2-b]pyran-3-yl ester