ethyl (2S,3S,E)-3-benzamido-6-oxo-2-[(E)-4-oxopent-2-enyl]hept-4-enoate

Base Information

• Chemical Name: ethyl (2S,3S,E)-3-benzamido-6-oxo-2-[(E)-4-oxopent-2-enyl]hept-4-enoate
• CAS No.: 1607805-86-6
• Molecular Formula: C₂₁H₂₅NO₅
• Molecular Weight: 371.433
• Mol file: 1607805-86-6.mol

Synonyms:ethyl (2S,3S,E)-3-benzamido-6-oxo-2-[(E)-4-oxopent-2-enyl]hept-4-enoate

Chemical Property of ethyl (2S,3S,E)-3-benzamido-6-oxo-2-[(E)-4-oxopent-2-enyl]hept-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2S,3S,E)-3-benzamido-6-oxo-2-[(E)-4-oxopent-2-enyl]hept-4-enoate

There total 8 articles about ethyl (2S,3S,E)-3-benzamido-6-oxo-2-[(E)-4-oxopent-2-enyl]hept-4-enoate 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:

ethyl (1S,2S)-2-benzamidocyclopent-3-enecarboxylate (1607805-67-3,634180-78-2) → ethyl (2S,3S,E)-3-benzamido-6-oxo-2-[(E)-4-oxopent-2-enyl]hept-4-enoate (1607805-86-6)

Guidance literature:

Multi-step reaction with 3 steps

1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone / 8 h / 20 °C

2: sodium periodate / water; tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3: tetrahydrofuran / 1 h / 20 °C

With sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; acetone; 3: |Wittig Olefination;

DOI:10.1002/ejoc.201301281

Reference yield:

6-Azabicyclo<3.2.0>hept-3-en-7-one (63838-48-2,97911-48-3,138127-85-2,146864-12-2) → ethyl (2S,3S,E)-3-benzamido-6-oxo-2-[(E)-4-oxopent-2-enyl]hept-4-enoate (1607805-86-6)

Guidance literature:

Multi-step reaction with 7 steps

1: Candida antarctica lipase B; water / tert-butyl methyl ether / 4.5 h / 80 °C / Resolution of racemate; Enzymatic reaction

2: thionyl chloride

3: water; sodium hydroxide / toluene / 1 h / 0 °C

4: sodium ethanolate / ethanol / 12 h / 0 °C

5: osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone / 8 h / 20 °C

6: sodium periodate / water; tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

7: tetrahydrofuran / 1 h / 20 °C

With Candida antarctica lipase B; sodium periodate; osmium(VIII) oxide; thionyl chloride; water; sodium ethanolate; 4-methylmorpholine N-oxide; sodium hydroxide; In tetrahydrofuran; ethanol; tert-butyl methyl ether; water; acetone; toluene; 7: |Wittig Olefination;

DOI:10.1002/ejoc.201301281

Reference yield:

ethyl (1R,2S)-2-benzamidocyclopent-3-enecarboxylate (1607805-66-2,634180-78-2) → ethyl (2S,3S,E)-3-benzamido-6-oxo-2-[(E)-4-oxopent-2-enyl]hept-4-enoate (1607805-86-6)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium ethanolate / ethanol / 12 h / 0 °C

2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / acetone / 8 h / 20 °C

3: sodium periodate / water; tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

4: tetrahydrofuran / 1 h / 20 °C

With sodium periodate; osmium(VIII) oxide; sodium ethanolate; 4-methylmorpholine N-oxide; In tetrahydrofuran; ethanol; water; acetone; 4: |Wittig Olefination;

DOI:10.1002/ejoc.201301281

upstream raw materials:

benzoyl chloride

C₈H₁₃NO₂

ethyl (1R,2S)-2-benzamidocyclopent-3-enecarboxylate

ethyl (1S,2S)-2-benzamidocyclopent-3-enecarboxylate

Downstream raw materials:

ethyl (2S,3S)-3-benzamido-6-oxo-2-(4-oxopentyl)heptanoate