(2R,5R,6R)-6-Ethyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (2R,5R,6R)-6-Ethyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 79252-31-6
• Molecular Formula: C₁₆H₁₆N₂O₆
• Molecular Weight: 332.313

Synonyms:(2R,5R,6R)-6-Ethyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property of (2R,5R,6R)-6-Ethyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

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Technology Process of (2R,5R,6R)-6-Ethyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

There total 16 articles about (2R,5R,6R)-6-Ethyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 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: 99.0%

4-(3-diazo-2-oxo-3-p-nitrobenzyloxycarbonylpropyl)-3-ethylazetidin-2-one → p-nitrobenzyl trans-6α-ethyl-3,7-dioxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (79252-31-6,84048-08-8,84621-82-9,91466-13-6,91466-14-7,91466-17-0,106036-69-5,112344-93-1,134309-74-3)

Guidance literature:

With rhodium(II) acetate; In benzene; at 80 ℃; for 0.5h;

DOI:10.1039/P19810002228

Reference yield: 84.0%

(3R,4R)-3-ethyl-4-<3-diazo-2-oxo-3-<<(p-nitrobenzyl)oxy>carbonyl>propyl>-2-azetidinone (83997-55-1) → (2R,5R,6R)-6-Ethyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (79252-31-6)

Guidance literature:

With rhodium(II) acetate; In benzene; for 0.75h; Heating;

DOI:10.1021/jo00238a041

Reference yield: 83.0%

((3R,4R)-3-Ethyl-2-oxo-4-phenylsulfanylcarbonylmethyl-azetidin-1-yl)-acetic acid 4-nitro-benzyl ester (92445-66-4,92445-67-5) → (2R,5R,6R)-6-Ethyl-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (79252-31-6)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.05h;

DOI:10.1016/S0040-4039(01)80262-8

upstream raw materials:

((3S,4R)-3-Ethyl-2-oxo-4-phenylsulfanylcarbonylmethyl-azetidin-1-yl)-acetic acid 4-nitro-benzyl ester

diethyl 2-ethyl-3-oxoglutarate

(2S,3R)-3-Amino-2-ethyl-pentanedioic acid

(2S,3R)-3-Amino-2-ethyl-pentanedioic acid 5-benzyl ester

Downstream raw materials:

(5RS,6RS)-p-nitrobenzyl 3-(2-acetamidoethylthio)-6-ethyl-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

p-Nitrobenzyl (5R,6R)-3-(2-acetamidoethylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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