4-[(2S,3R)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-phenyl ester

Base Information

• Chemical Name: 4-[(2S,3R)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-phenyl ester
• CAS No.: 77171-46-1
• Molecular Formula: C₁₅H₁₆N₂O₇
• Molecular Weight: 336.301

Synonyms:4-[(2S,3R)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-phenyl ester

Chemical Property of 4-[(2S,3R)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-phenyl ester

Chemical Property:

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Technology Process of 4-[(2S,3R)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-phenyl ester

There total 20 articles about 4-[(2S,3R)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-phenyl 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: 33.0%

magnesium 4-nitrobenzyl malonate (105995-50-4) + [(2S,3R)-3-(1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetic acid (78501-85-6,95672-33-6,115938-28-8,115938-29-9) → 4-[(2S,3R)-3-(1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester (75321-07-2,77171-45-0,77171-46-1,81846-30-2,84985-43-3,90192-01-1,96392-38-0)

Guidance literature:

With 1,1'-carbonyldiimidazole; In tetrahydrofuran; for 4h; Ambient temperature;

Reference yield:

propanedioic acid mono[(4-nitrophenyl)methyl] ester (77359-11-6) + (trans-(2RS,3SR)-3-<(1SR)-hydroxyethyl>-4-oxoazetidin-2-yl) acetic acid (78501-85-6) + 1,1'-carbonyldiimidazole (530-62-1) → 4-[(2S,3R)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-phenyl ester (77171-46-1)

Guidance literature:

Yield given. Multistep reaction; 1.) acetonitrile, dimethylformamide, 0 deg C, 50 min;

DOI:10.1021/ja00333a053

Reference yield:

4-[(2S,3R)-3-((S)-1-Formyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester (79543-87-6,84985-45-5) → 4-[(2S,3R)-3-((S)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester (75321-07-2,77171-45-0,77171-46-1,81846-30-2,84985-43-3,90192-01-1,96392-38-0)

Guidance literature:

With hydrogenchloride; In methanol; water; at 25 ℃; for 1.5h;

DOI:10.1016/S0040-4039(00)78606-0

upstream raw materials:

4-[(2S,3R)-3-((S)-1-Formyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester

(E)-2-Acetyl-3-benzylamino-pent-2-enedioic acid diethyl ester

(2R,3S)-3-Benzylamino-2-((R)-1-hydroxy-ethyl)-pentanedioic acid diethyl ester

benzyl -4-oxoazetidin-2-yl> acetate

Downstream raw materials:

(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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

(5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

4-[(2S,3R)-3-((S)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester

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