(5R,6S,7R)-ethyl 6,7-epoxy-2-phenyl-2,4,9-triazabicyclo[4.3.0]nonane-1,3-dione-5-carboxylate

Base Information

Chemical Name:(5R,6S,7R)-ethyl 6,7-epoxy-2-phenyl-2,4,9-triazabicyclo[4.3.0]nonane-1,3-dione-5-carboxylate
CAS No.:1345970-33-3
Molecular Formula:C₁₅H₁₅N₃O₅
Molecular Weight:317.301
Hs Code.:

Synonyms:(5R,6S,7R)-ethyl 6,7-epoxy-2-phenyl-2,4,9-triazabicyclo[4.3.0]nonane-1,3-dione-5-carboxylate

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Chemical Property of (5R,6S,7R)-ethyl 6,7-epoxy-2-phenyl-2,4,9-triazabicyclo[4.3.0]nonane-1,3-dione-5-carboxylate

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Technology Process of (5R,6S,7R)-ethyl 6,7-epoxy-2-phenyl-2,4,9-triazabicyclo[4.3.0]nonane-1,3-dione-5-carboxylate

There total 4 articles about (5R,6S,7R)-ethyl 6,7-epoxy-2-phenyl-2,4,9-triazabicyclo[4.3.0]nonane-1,3-dione-5-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: 60.0%

: 1345970-31-1
(R)-ethyl 2-phenyl-2,4,9-triazabicyclo[4.3.0]non-6-ene-1,3-dione-5-carboxylate

: 1345970-33-3
(5R,6S,7R)-ethyl 6,7-epoxy-2-phenyl-2,4,9-triazabicyclo[4.3.0]nonane-1,3-dione-5-carboxylate

: (5R,6R,7S)-ethyl 6,7-epoxy-2-phenyl-2,4,9-triazabicyclo[4.3.0]nonane-1,3-dione-5-carboxylate

Guidance literature:: With oxone; sodium hydrogencarbonate; In 1,1,1-trifluoro-2-propanone; water; acetonitrile; at 0 - 20 ℃; for 22h; optical yield given as %de;
DOI:10.1021/jo201486q

Reference yield:

: 1345970-28-6
ethyl 5-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-2,4-pentadienoate

: 1345970-33-3
(5R,6S,7R)-ethyl 6,7-epoxy-2-phenyl-2,4,9-triazabicyclo[4.3.0]nonane-1,3-dione-5-carboxylate

: (5R,6R,7S)-ethyl 6,7-epoxy-2-phenyl-2,4,9-triazabicyclo[4.3.0]nonane-1,3-dione-5-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: dichloromethane / 0.5 h

2: triethylamine; p-Chlorothiophenol / methanol / 0.67 h / 0 - 20 °C

3: triethylsilane; trifluoroacetic acid / dichloromethane / 5 h / 20 °C

4: oxone; sodium hydrogencarbonate / 1,1,1-trifluoro-2-propanone; water; acetonitrile / 22 h / 0 - 20 °C

With triethylsilane; oxone; sodium hydrogencarbonate; triethylamine; p-Chlorothiophenol; trifluoroacetic acid; In methanol; dichloromethane; 1,1,1-trifluoro-2-propanone; water; acetonitrile; 1: Diels-Alder cycloaddition;
DOI:10.1021/jo201486q

Reference yield:

: 1345970-29-7
(5S,8S)-ethyl 8-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyloxy)-2-phenyl-2,4,9-triazabicyclo[4.3.0]non-6-ene-1,3-dione-5-carboxylate

: 1345970-33-3
(5R,6S,7R)-ethyl 6,7-epoxy-2-phenyl-2,4,9-triazabicyclo[4.3.0]nonane-1,3-dione-5-carboxylate

: (5R,6R,7S)-ethyl 6,7-epoxy-2-phenyl-2,4,9-triazabicyclo[4.3.0]nonane-1,3-dione-5-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine; p-Chlorothiophenol / methanol / 0.67 h / 0 - 20 °C

2: triethylsilane; trifluoroacetic acid / dichloromethane / 5 h / 20 °C

3: oxone; sodium hydrogencarbonate / 1,1,1-trifluoro-2-propanone; water; acetonitrile / 22 h / 0 - 20 °C

With triethylsilane; oxone; sodium hydrogencarbonate; triethylamine; p-Chlorothiophenol; trifluoroacetic acid; In methanol; dichloromethane; 1,1,1-trifluoro-2-propanone; water; acetonitrile;
DOI:10.1021/jo201486q