(3S,4S)-ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate

Base Information

• Chemical Name: (3S,4S)-ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate
• CAS No.: 1439359-08-6
• Molecular Formula: C₁₈H₂₀N₂O₄
• Molecular Weight: 328.368
• Mol file: 1439359-08-6.mol

Synonyms:

Chemical Property of (3S,4S)-ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate

There total 3 articles about (3S,4S)-ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate 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:

(E)-3-phenylpropenal (14371-10-9) + ethanol (64-17-5) + 3-(2-nitroethenyl)pyridine (3156-52-3) → (3S,4S)-ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate (1439359-08-6) + ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate + (3R,4R)-ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate

Guidance literature:

With C₂₃H₃₃F₅N₃OSi⁽¹⁺⁾*BF₄^(1-); sodium acetate; In ethanol; at 23 ℃; for 12h; Overall yield = 73%; stereoselective reaction; Inert atmosphere;

DOI:10.1021/ja403847e

Reference yield:

rac-2-nitro-1-(pyridin-3-yl)ethan-1-ol (101861-30-7) → (3S,4S)-ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate (1439359-08-6) + ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate + (3R,4R)-ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic anhydride; triethylamine / 3 h / 0 - 20 °C / Inert atmosphere

2: sodium acetate; C₂₃H₃₃F₅N₃OSi⁽¹⁺⁾*BF₄^(1-) / ethanol / 12 h / 23 °C / Inert atmosphere

With C₂₃H₃₃F₅N₃OSi⁽¹⁺⁾*BF₄^(1-); sodium acetate; triethylamine; trifluoroacetic anhydride; In ethanol;

DOI:10.1021/ja403847e

Reference yield:

3-pyridinecarboxaldehyde (500-22-1) → (3S,4S)-ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate (1439359-08-6) + ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate + (3R,4R)-ethyl 5-nitro-3-phenyl-4-(pyridin-3-yl)pentanoate

Guidance literature:

Multi-step reaction with 3 steps

1: potassium tert-butylate / tetrahydrofuran; tert-butyl alcohol / 13 h / 0 - 20 °C / Inert atmosphere

2: trifluoroacetic anhydride; triethylamine / 3 h / 0 - 20 °C / Inert atmosphere

3: sodium acetate; C₂₃H₃₃F₅N₃OSi⁽¹⁺⁾*BF₄^(1-) / ethanol / 12 h / 23 °C / Inert atmosphere

With C₂₃H₃₃F₅N₃OSi⁽¹⁺⁾*BF₄^(1-); potassium tert-butylate; sodium acetate; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; ethanol; tert-butyl alcohol;

DOI:10.1021/ja403847e

upstream raw materials:

rac-2-nitro-1-(pyridin-3-yl)ethan-1-ol

3-pyridinecarboxaldehyde

(E)-3-phenylpropenal

ethanol

Refernces