(3SR,4RS)-3-[(RS)-1-hydroxyethyl]-β,2-dioxo-4-azetidinebutanoic acid p-nitrobenzyl ester

Base Information

Chemical Name:(3SR,4RS)-3-[(RS)-1-hydroxyethyl]-β,2-dioxo-4-azetidinebutanoic acid p-nitrobenzyl ester
CAS No.:81846-30-2
Molecular Formula:C₁₆H₁₈N₂O₇
Molecular Weight:350.328
Hs Code.:

Synonyms:(3SR,4RS)-3-[(RS)-1-hydroxyethyl]-β,2-dioxo-4-azetidinebutanoic acid p-nitrobenzyl ester

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Chemical Property of (3SR,4RS)-3-[(RS)-1-hydroxyethyl]-β,2-dioxo-4-azetidinebutanoic acid p-nitrobenzyl ester

Chemical Property:

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Technology Process of (3SR,4RS)-3-[(RS)-1-hydroxyethyl]-β,2-dioxo-4-azetidinebutanoic acid p-nitrobenzyl ester

There total 22 articles about (3SR,4RS)-3-[(RS)-1-hydroxyethyl]-β,2-dioxo-4-azetidinebutanoic acid p-nitrobenzyl 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%

: 105995-50-4
magnesium 4-nitrobenzyl malonate

: 78501-85-6,95672-33-6,115938-28-8,115938-29-9
[(2S,3R)-3-(1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetic acid

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

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

Reference yield:

: 79543-87-6,84985-45-5
4-[(2S,3R)-3-((S)-1-Formyloxy-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
4-[(2S,3R)-3-((S)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester

Guidance literature:: With hydrogenchloride; In methanol; water; at 25 ℃; for 1.5h;
DOI:10.1016/S0040-4039(00)78606-0

Reference yield:

: 77120-91-3
(E)-2-Acetyl-3-benzylamino-pent-2-enedioic acid diethyl ester

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

Guidance literature:: Multi-step reaction with 11 steps

1: NaBH₃CN / acetic acid

2: cc. HCl / Heating

3: hydrogen / Pd(OH)2/C / acetic acid / 2068.6 Torr

4: AcOH / 16 h / 70 °C

5: 92 percent / NEt₃, DCC / acetonitrile / 4 h / 60 °C

6: NEt₃ / dimethylformamide

7: hydrogen / Pd/c / 2068.6 Torr

8: 1.) carbonyldiimidazol, 4-dimethylaminopyridine / 1.) CH₂Cl₂ 2.) CH₃CN, reflux

9: HCl / methanol; H₂O

10: Triphenylphosphine, diisopropylazodicarboxylate, / THF, 25 deg C, 1 h

11: HCl / methanol; H₂O / 1.5 h / 25 °C

With hydrogenchloride; dmap; Carbonyldiimidazole; di-isopropyl azodicarboxylate; hydrogen; sodium cyanoborohydride; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; palladium dihydroxide; palladium on activated charcoal; acetic acid; In methanol; water; acetic acid; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(00)78606-0