Acetoxy-[(3S,4R)-2-oxo-4-pent-3-ynyl-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester

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Chemical Name:Acetoxy-[(3S,4R)-2-oxo-4-pent-3-ynyl-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester
CAS No.:200420-87-7
Molecular Formula:C₂₇H₂₇N₃O₉
Molecular Weight:537.526
Hs Code.:

Synonyms:Acetoxy-[(3S,4R)-2-oxo-4-pent-3-ynyl-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester

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Chemical Property of Acetoxy-[(3S,4R)-2-oxo-4-pent-3-ynyl-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester

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Technology Process of Acetoxy-[(3S,4R)-2-oxo-4-pent-3-ynyl-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester

There total 10 articles about Acetoxy-[(3S,4R)-2-oxo-4-pent-3-ynyl-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic 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:

: 10229-10-4
pent-3-yn-1-ol

: 200420-87-7
Acetoxy-[(3S,4R)-2-oxo-4-pent-3-ynyl-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 30 min

3: 1.7 g / conc. HCl / tetrahydrofuran / 0.5 h / Ambient temperature

4: LiAl(t-BuO)3H / tetrahydrofuran / 0.75 h / 0 °C

5: 4A molecular sieves / dimethylformamide; toluene / 8 h / Heating

6: pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; 4 A molecular sieve; lithium tri-t-butoxyaluminum hydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo971433w

Reference yield:

: 54106-83-1
pent-3-ynyl triflate

: 200420-87-7
Acetoxy-[(3S,4R)-2-oxo-4-pent-3-ynyl-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) LDA / 1.) THF, -78 deg C, 30 min, 2.) -78 deg C, 30 min

2: 1.7 g / conc. HCl / tetrahydrofuran / 0.5 h / Ambient temperature

3: LiAl(t-BuO)3H / tetrahydrofuran / 0.75 h / 0 °C

4: 4A molecular sieves / dimethylformamide; toluene / 8 h / Heating

5: pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

With pyridine; hydrogenchloride; 4 A molecular sieve; lithium tri-t-butoxyaluminum hydride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo971433w

Reference yield:

: 83654-96-0
p-nitrobenzyl glyoxylate monohydrate

: 200420-87-7
Acetoxy-[(3S,4R)-2-oxo-4-pent-3-ynyl-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-acetic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 4A molecular sieves / dimethylformamide; toluene / 8 h / Heating

2: pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

With pyridine; 4 A molecular sieve; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo971433w