(3S,4R)-1-<(tert-butoxycarbonyl)methyl>-3-<(S)-4-phenyloxazolidinyl>-4-phenylazetidin-2-one

Base Information

• Chemical Name: (3S,4R)-1-<(tert-butoxycarbonyl)methyl>-3-<(S)-4-phenyloxazolidinyl>-4-phenylazetidin-2-one
• CAS No.: 123932-09-2
• Molecular Formula: C₂₄H₂₆N₂O₅
• Molecular Weight: 422.481

Synonyms:(3S,4R)-1-<(tert-butoxycarbonyl)methyl>-3-<(S)-4-phenyloxazolidinyl>-4-phenylazetidin-2-one

Chemical Property of (3S,4R)-1-<(tert-butoxycarbonyl)methyl>-3-<(S)-4-phenyloxazolidinyl>-4-phenylazetidin-2-one

Chemical Property:

Purity/Quality:

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Technology Process of (3S,4R)-1-<(tert-butoxycarbonyl)methyl>-3-<(S)-4-phenyloxazolidinyl>-4-phenylazetidin-2-one

There total 5 articles about (3S,4R)-1-<(tert-butoxycarbonyl)methyl>-3-<(S)-4-phenyloxazolidinyl>-4-phenylazetidin-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: 83.0%

tert-butyl N-benzylideneglycinate (64923-12-2) + (S)-(4-phenyloxazolidinyl)ketene (108493-67-0) → (3S,4R)-1-<(tert-butoxycarbonyl)methyl>-3-<(S)-4-phenyloxazolidinyl>-4-phenylazetidin-2-one (123932-09-2)

Guidance literature:

In dichloromethane; -78 deg C to RT;

DOI:10.1021/ja00158a041

Reference yield:

Glycine tert-butyl ester (6456-74-2) → (3S,4R)-1-<(tert-butoxycarbonyl)methyl>-3-<(S)-4-phenyloxazolidinyl>-4-phenylazetidin-2-one (123932-09-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / sodium sulfate / benzene / Ambient temperature

2: 83 percent / CH₂Cl₂ / -78 deg C to RT

With sodium sulfate; In dichloromethane; benzene;

DOI:10.1021/ja00158a041

Reference yield:

2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetic acid (123882-32-6,136861-61-5,99333-54-7) → (3S,4R)-1-<(tert-butoxycarbonyl)methyl>-3-<(S)-4-phenyloxazolidinyl>-4-phenylazetidin-2-one (123932-09-2)

Guidance literature:

Multi-step reaction with 3 steps

1: oxalyl chloride, DMF / toluene / 5 h / 60 °C

2: triethylamine / CH₂Cl₂ / 0.5 h / -78 °C

3: 83 percent / CH₂Cl₂ / -78 deg C to RT

With oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; In dichloromethane; toluene;

DOI:10.1021/ja00158a041

upstream raw materials:

tert-butyl N-benzylideneglycinate

(S)-(4-phenyloxazolidinyl)ketene

Glycine tert-butyl ester

2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetic acid

Downstream raw materials:

(3S,4R,1'R)-1-<1'-(tert-butoxycarbonyl)-2'-phenylethyl>-3-<(S)-4-phenyloxazolidinyl>-4-phenylazetidin-2-one

(S)-2-[(3S,4R)-2-Oxo-3-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-4-phenyl-azetidin-1-yl]-3-phenyl-propionic acid tert-butyl ester

(3S,4R,1'R)-1-<1'-(tert-butoxycarbonyl)buten-3-yl>-3-<(S)-4-phenyloxazolidinyl>-4-phenylazetidin-2-one

(S)-2-[(3S,4R)-2-Oxo-3-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-4-phenyl-azetidin-1-yl]-pent-4-enoic acid tert-butyl ester

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