(5RS,6SR)-1-Methyl-3-oxa-5-hydroxy-6-cinnamoyl-6-methoxy-2-piperidinone

Base Information

• Chemical Name: (5RS,6SR)-1-Methyl-3-oxa-5-hydroxy-6-cinnamoyl-6-methoxy-2-piperidinone
• CAS No.: 73062-02-9
• Molecular Formula: C₁₅H₁₇NO₅
• Molecular Weight: 291.304
• Mol file: 73062-02-9.mol

Synonyms:(5RS,6SR)-1-Methyl-3-oxa-5-hydroxy-6-cinnamoyl-6-methoxy-2-piperidinone

Chemical Property of (5RS,6SR)-1-Methyl-3-oxa-5-hydroxy-6-cinnamoyl-6-methoxy-2-piperidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5RS,6SR)-1-Methyl-3-oxa-5-hydroxy-6-cinnamoyl-6-methoxy-2-piperidinone

There total 1 articles about (5RS,6SR)-1-Methyl-3-oxa-5-hydroxy-6-cinnamoyl-6-methoxy-2-piperidinone 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: 50.0%

2-Oxoethyl (1-methoxy-2-oxo-4-phenyl-3(E)-butenyl)-N-methylcarbamate (73062-01-8) → (4RS,5SR)-1-Methyl-3-oxa-4-hydroxymethyl-5-cinnamoyl-5-methoxy-2-pyrrolidinone (73062-06-3) + (5RS,6SR)-1-Methyl-3-oxa-5-hydroxy-6-cinnamoyl-6-methoxy-2-piperidinone (73062-02-9) + (5SR,6SR)-1-Methyl-3-oxa-5-hydroxy-6-cinnamoyl-6-methoxy-2-piperidinone (73089-34-6)

Guidance literature:

With potassium carbonate; In methanol; at 25 ℃; for 3.5h; Product distribution; Other reaction times;

DOI:10.1021/jo01296a021

Reference yield: 57.0%

trifluoromethylsulfonic anhydride (358-23-6) + (5RS,6SR)-1-Methyl-3-oxa-5-hydroxy-6-cinnamoyl-6-methoxy-2-piperidinone (73062-02-9) → Trifluoro-methanesulfonic acid (4S,5R)-4-methoxy-3-methyl-2-oxo-4-[(E)-(3-phenyl-acryloyl)]-[1,3]oxazinan-5-yl ester (73062-05-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -70 ℃; for 0.75h;

DOI:10.1021/jo01296a021

Reference yield:

(5RS,6SR)-1-Methyl-3-oxa-5-hydroxy-6-cinnamoyl-6-methoxy-2-piperidinone (73062-02-9) → 1-Methyl-3-oxa-6-cinnamoyl-6-methoxy-2-piperidinone (73062-27-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 57 percent / Diisopropylethylamine / CH₂Cl₂ / 0.75 h / -70 °C

2: 38.8 mg / NaI / acetone / 18 h / 25 °C

3: 68 percent / Azobis(isobutyronitrile), tri-n-butyltin hydride / benzene / 9 h / 55 °C

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; N-ethyl-N,N-diisopropylamine; sodium iodide; In dichloromethane; acetone; benzene;

DOI:10.1021/jo01296a021

upstream raw materials:

2-Oxoethyl (1-methoxy-2-oxo-4-phenyl-3(E)-butenyl)-N-methylcarbamate

Downstream raw materials:

Trifluoro-methanesulfonic acid (4S,5R)-4-methoxy-3-methyl-2-oxo-4-[(E)-(3-phenyl-acryloyl)]-[1,3]oxazinan-5-yl ester

(5RS,6SR)-1-Methyl-3-oxa-5-acetoxy-6-cinnamoyl-6-methoxy-2-piperidinone

1-Methyl-3-oxa-6-cinnamoyl-6-methoxy-2-piperidinone

(5SR,6RS)-1-Methyl-3-oxa-5-iodo-6-cinnamoyl-6-methoxy-2-piperidinone