(-)-3β-((1S)-1-hydroxyethyl)-4α-<3-<<(p-nitrobenzyl)oxy>carbonyl>-2-oxopropyl>azetidin-2-one

Base Information

Chemical Name:(-)-3β-((1S)-1-hydroxyethyl)-4α-<3-<<(p-nitrobenzyl)oxy>carbonyl>-2-oxopropyl>azetidin-2-one
CAS No.:96392-38-0
Molecular Formula:C₁₆H₁₈N₂O₇
Molecular Weight:350.328
Hs Code.:

Synonyms:(-)-3β-((1S)-1-hydroxyethyl)-4α-<3-<<(p-nitrobenzyl)oxy>carbonyl>-2-oxopropyl>azetidin-2-one

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Chemical Property of (-)-3β-((1S)-1-hydroxyethyl)-4α-<3-<<(p-nitrobenzyl)oxy>carbonyl>-2-oxopropyl>azetidin-2-one

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Technology Process of (-)-3β-((1S)-1-hydroxyethyl)-4α-<3-<<(p-nitrobenzyl)oxy>carbonyl>-2-oxopropyl>azetidin-2-one

There total 26 articles about (-)-3β-((1S)-1-hydroxyethyl)-4α-<3-<<(p-nitrobenzyl)oxy>carbonyl>-2-oxopropyl>azetidin-2-one 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: 79.8%

: 96392-36-8
(-)-3β-<(1S)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-4α-<3-<<(p-nitrobenzyl)oxy>carbonyl>-2,2-(ethylenedioxy)propyl>azetidin-2-one

: 96392-38-0
(-)-3β-((1S)-1-hydroxyethyl)-4α-<3-<<(p-nitrobenzyl)oxy>carbonyl>-2-oxopropyl>azetidin-2-one

Guidance literature:: With hydrogenchloride; In methanol; at 5 ℃; for 2h;
DOI:10.1021/jo00213a025

Reference yield:

: 32296-85-8
ethyl 3,3-(ethylenedioxy)-4-formylbutyrate

: 96392-38-0
(-)-3β-((1S)-1-hydroxyethyl)-4α-<3-<<(p-nitrobenzyl)oxy>carbonyl>-2-oxopropyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: benzene / 1 h / 50 °C

2: benzene / 16 h / Heating

3: H₂, AcOH / 10percent Pd/C / 38 h / 3420 Torr / Ambient temperature

4: N,N'-dicyclohexylcarbodiimide / acetonitrile / 3 h / 60 °C

5: 52 percent / Et₃N / dimethylformamide / 18 h / Ambient temperature

6: 1.) aq. NaOH / 1.) THF, RT, 2 h, 2.) DMF, RT, 2 h

7: 79.8 percent / conc. hydrochloric acid / methanol / 2 h / 5 °C

With hydrogenchloride; sodium hydroxide; hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; acetonitrile; benzene;
DOI:10.1021/jo00213a025

Reference yield:

: 96326-23-7
benzyl (+)-(3,4-cis,4,5-trans)-3-<3-(ethoxycarbonyl)-2,2-(ethylenedioxy)propyl>-5-methyl-2-((1R)-1-phenylethyl)isoxazolidine-4-carboxylate

: 96392-38-0
(-)-3β-((1S)-1-hydroxyethyl)-4α-<3-<<(p-nitrobenzyl)oxy>carbonyl>-2-oxopropyl>azetidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: H₂, AcOH / 10percent Pd/C / 38 h / 3420 Torr / Ambient temperature

2: N,N'-dicyclohexylcarbodiimide / acetonitrile / 3 h / 60 °C

3: 52 percent / Et₃N / dimethylformamide / 18 h / Ambient temperature

4: 1.) aq. NaOH / 1.) THF, RT, 2 h, 2.) DMF, RT, 2 h

5: 79.8 percent / conc. hydrochloric acid / methanol / 2 h / 5 °C

With hydrogenchloride; sodium hydroxide; hydrogen; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00213a025