(2R,3R,4R)-2-ethyl 4-methyl 3-(4-cyanophenyl)-5-oxotetrahydrofuran-2,4-dicarboxylate

Base Information

Chemical Name:(2R,3R,4R)-2-ethyl 4-methyl 3-(4-cyanophenyl)-5-oxotetrahydrofuran-2,4-dicarboxylate
CAS No.:1373610-51-5
Molecular Formula:C₁₆H₁₅NO₆
Molecular Weight:317.298
Hs Code.:

Synonyms:(2R,3R,4R)-2-ethyl 4-methyl 3-(4-cyanophenyl)-5-oxotetrahydrofuran-2,4-dicarboxylate

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Chemical Property of (2R,3R,4R)-2-ethyl 4-methyl 3-(4-cyanophenyl)-5-oxotetrahydrofuran-2,4-dicarboxylate

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Technology Process of (2R,3R,4R)-2-ethyl 4-methyl 3-(4-cyanophenyl)-5-oxotetrahydrofuran-2,4-dicarboxylate

There total 3 articles about (2R,3R,4R)-2-ethyl 4-methyl 3-(4-cyanophenyl)-5-oxotetrahydrofuran-2,4-dicarboxylate 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: 88.0%

: 1373610-35-5
3-ethyl 1,1-dimethyl 2-(4-cyanophenyl)-3-oxopropane-1,1,3-tricarboxylate

: 1373610-51-5
(2R,3R,4R)-2-ethyl 4-methyl 3-(4-cyanophenyl)-5-oxotetrahydrofuran-2,4-dicarboxylate

Guidance literature:: With formic acid; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; C₄₀H₃₂N₂O₂S; triethylamine; In N,N-dimethyl-formamide; at 20 - 70 ℃; for 16.5h; optical yield given as %ee; stereoselective reaction; Inert atmosphere; Resolution of racemate;
DOI:10.1021/ja3027136

Reference yield:

: 1373610-35-5
3-ethyl 1,1-dimethyl 2-(4-cyanophenyl)-3-oxopropane-1,1,3-tricarboxylate

: 1373610-51-5
(2R,3R,4R)-2-ethyl 4-methyl 3-(4-cyanophenyl)-5-oxotetrahydrofuran-2,4-dicarboxylate

: C₁₆H₁₅NO₆

Guidance literature:: With formic acid; C₄₀H₃₂N₂O₂S; [RuCl₂(p-cymene)]₂; triethylamine; In N,N-dimethyl-formamide; at 75 ℃; stereoselective reaction;
DOI:10.1021/jacs.5b00787

Reference yield:

: 93098-69-2
2–(4–cyanobenzylidene)dimethyl malonate

: 1373610-51-5
(2R,3R,4R)-2-ethyl 4-methyl 3-(4-cyanophenyl)-5-oxotetrahydrofuran-2,4-dicarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; triethylamine / toluene / 16 h / 20 °C / Inert atmosphere

2: [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; formic acid; C40H32N2O2S; triethylamine / N,N-dimethyl-formamide / 16.5 h / 20 - 70 °C / Inert atmosphere; Resolution of racemate

With 2-phenyl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate; formic acid; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; C₄₀H₃₂N₂O₂S; triethylamine; In N,N-dimethyl-formamide; toluene; 1: Stetter reaction;
DOI:10.1021/ja3027136