ethyl (1R,2S,3S)-2-cyano-3-(2-oxoethyl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-carboxylate

Base Information

• Chemical Name: ethyl (1R,2S,3S)-2-cyano-3-(2-oxoethyl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-carboxylate
• CAS No.: 1279108-79-0
• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.354
• Mol file: 1279108-79-0.mol

Synonyms:ethyl (1R,2S,3S)-2-cyano-3-(2-oxoethyl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-carboxylate

Chemical Property of ethyl (1R,2S,3S)-2-cyano-3-(2-oxoethyl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (1R,2S,3S)-2-cyano-3-(2-oxoethyl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-carboxylate

There total 5 articles about ethyl (1R,2S,3S)-2-cyano-3-(2-oxoethyl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-carboxylate 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: 87.0%

2,4-hexadienal (80466-34-8,4488-48-6) + ethyl benzylidenecyanoacetate (2025-40-3) → C18H19NO3 + C18H19NO3 + ethyl (1R,2S,3S)-2-cyano-3-(2-oxoethyl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-carboxylate (1279108-79-0)

Guidance literature:

With 4-Fluorobenzoic acid; C₄₁H₆₉NO₃Si; In chloroform; at 50 ℃; for 48h; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ja1112194

Reference yield: 73.0%

2,4-hexadienal (80466-34-8,4488-48-6) + ethyl benzylidenecyanoacetate (2025-40-3) → ethyl (1R,2S,3S)-2-cyano-3-(2-oxoethyl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-carboxylate (1279108-79-0)

Guidance literature:

With (L)-2-{diphenyl[(triphenylsilyl)oxy]methyl}pyrrolidine; In toluene; at 70 ℃; for 60h; enantioselective reaction; Catalytic behavior;

DOI:10.1016/j.bmcl.2020.127063

Reference yield:

2,4-hexadienal (80466-34-8,4488-48-6) + ethyl benzylidenecyanoacetate (2025-40-3) → C18H19NO3 + ethyl (1R,2S,3S)-2-cyano-3-(2-oxoethyl)-1,2,3,6-tetrahydro-[1,1'-biphenyl]-2-carboxylate (1279108-79-0)

Guidance literature:

With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; In toluene; at 70 ℃; for 60h; Reagent/catalyst; Overall yield = 75 percent; enantioselective reaction; Catalytic behavior;

DOI:10.1016/j.bmcl.2020.127063

upstream raw materials:

2,4-hexadienal

ethyl benzylidenecyanoacetate

trans,trans-2,4-Hexadienal

ethyl (E)-2-cyano-3-phenyl-2-propenoate