ethyl (1S,2R,3S,5R)-2-benzamido-3,5-di(3’-oxobutyl)cyclopentanecarboxylate

Base Information

• Chemical Name: ethyl (1S,2R,3S,5R)-2-benzamido-3,5-di(3’-oxobutyl)cyclopentanecarboxylate
• CAS No.: 1446558-44-6
• Molecular Formula: C₂₃H₃₁NO₅
• Molecular Weight: 401.503
• Mol file: 1446558-44-6.mol

Synonyms:ethyl (1S,2R,3S,5R)-2-benzamido-3,5-di(3’-oxobutyl)cyclopentanecarboxylate

Chemical Property of ethyl (1S,2R,3S,5R)-2-benzamido-3,5-di(3’-oxobutyl)cyclopentanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (1S,2R,3S,5R)-2-benzamido-3,5-di(3’-oxobutyl)cyclopentanecarboxylate

There total 8 articles about ethyl (1S,2R,3S,5R)-2-benzamido-3,5-di(3’-oxobutyl)cyclopentanecarboxylate 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: 86.0%

ethyl (1S,2R,3R,5S)-2-benzamido-3,5-di((E)-3-oxobut-1-enyl)cyclopentanecarboxylate (1446558-42-4) → ethyl (1S,2R,3S,5R)-2-benzamido-3,5-di(3’-oxobutyl)cyclopentanecarboxylate (1446558-44-6)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 1h; enantioselective reaction;

DOI:10.1002/chem.201203183

Reference yield:

diexo-3-Aza-4-oxotricyclo<4.2.1.02,5>non-7-ene (14735-70-7,14805-31-3,924272-78-6,670221-11-1) → ethyl (1S,2R,3S,5R)-2-benzamido-3,5-di(3’-oxobutyl)cyclopentanecarboxylate (1446558-44-6)

Guidance literature:

Multi-step reaction with 7 steps

1: water / 168 h / 70 °C / Enzymatic reaction

2: hydrogenchloride / 0 °C

3: sodium hydrogencarbonate / toluene / 0 °C

4: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone / 12 h / 20 °C

5: sodium periodate / water; tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

6: tetrahydrofuran / 1.16 h / 0 - 20 °C

7: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 1 h / 20 °C

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; 5%-palladium/activated carbon; water; hydrogen; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; ethyl acetate; acetone; toluene; 6: |Wittig Rearrangement;

DOI:10.1002/chem.201203183

Reference yield:

(1R,2R,5S,6S)-3-azatricyclo[4.2.1.02,5]non-7-en-4-one (924272-78-6,670221-11-1) → ethyl (1S,2R,3S,5R)-2-benzamido-3,5-di(3’-oxobutyl)cyclopentanecarboxylate (1446558-44-6)

Guidance literature:

Multi-step reaction with 6 steps

1: hydrogenchloride / 0 °C

2: sodium hydrogencarbonate / toluene / 0 °C

3: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone / 12 h / 20 °C

4: sodium periodate / water; tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

5: tetrahydrofuran / 1.16 h / 0 - 20 °C

6: 5%-palladium/activated carbon; hydrogen / ethyl acetate / 1 h / 20 °C

With hydrogenchloride; sodium periodate; osmium(VIII) oxide; 5%-palladium/activated carbon; hydrogen; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; ethyl acetate; acetone; toluene; 5: |Wittig Rearrangement;

DOI:10.1002/chem.201203183

upstream raw materials:

diexo-3-Aza-4-oxotricyclo<4.2.1.0^2,5>non-7-ene

(1R,2R,5S,6S)-3-azatricyclo[4.2.1.0^2,5]non-7-en-4-one

C₁₀H₁₅NO₂*ClH

ethyl (1S,2S,3R,4R)-3-benzamidobicyclo[2.2.1]hept-5-ene-2-carboxylate