(2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxaldehyde

Base Information

• Chemical Name: (2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxaldehyde
• CAS No.: 161806-13-9
• Molecular Formula: C₂₀H₃₁NO₄Si
• Molecular Weight: 377.556
• Mol file: 161806-13-9.mol

Synonyms:(2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxaldehyde

Chemical Property of (2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxaldehyde

There total 8 articles about (2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxaldehyde 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:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxaldehyde (161806-13-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / imidazole / dimethylformamide / Ambient temperature

2: m-CPBA / CH₂Cl₂

3: 1.) (CF₃CO)2O, 2,6-lutidine, 2.) aq. NaHCO₃ / 1.) CH₂Cl₂, r.t., 1 h, 2.) 30 min

With 1H-imidazole; 2,6-dimethylpyridine; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00110a035

Reference yield:

(3S,4S)-3-<(R)-1-(Formyloxy)ethyl>-1-<(4-methoxyphenyl)methyl>-4-<(phenylthio)methyl>-2-azetidinone (161806-11-7) → (2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxaldehyde (161806-13-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / 10percent aq. HCl / methanol / 4 h / Ambient temperature

2: 90 percent / imidazole / dimethylformamide / Ambient temperature

3: m-CPBA / CH₂Cl₂

4: 1.) (CF₃CO)2O, 2,6-lutidine, 2.) aq. NaHCO₃ / 1.) CH₂Cl₂, r.t., 1 h, 2.) 30 min

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00110a035

Reference yield:

(3S,4S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-<(phenylthio)methyl>-2-azetidinone (161806-12-8) → (2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxaldehyde (161806-13-9)

Guidance literature:

Multi-step reaction with 2 steps

1: m-CPBA / CH₂Cl₂

2: 1.) (CF₃CO)2O, 2,6-lutidine, 2.) aq. NaHCO₃ / 1.) CH₂Cl₂, r.t., 1 h, 2.) 30 min

With 2,6-dimethylpyridine; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In dichloromethane;

DOI:10.1021/jo00110a035

upstream raw materials:

tert-butyldimethylsilyl chloride

(3S,4S)-3-<(R)-1-(Formyloxy)ethyl>-1-<(4-methoxyphenyl)methyl>-4-<(phenylthio)methyl>-2-azetidinone

(3S,4S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-<(phenylthio)methyl>-2-azetidinone

(3S,4S)-3-<(S)-1-Hydroxyethyl>-1-<(4-methoxyphenyl)methyl>-4-<(phenylthio)methyl>-2-azetidinone

Downstream raw materials:

(2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxylic acid