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

Base Information

• Chemical Name: (2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxylic acid
• CAS No.: 102679-24-3
• Molecular Formula: C₂₀H₃₁NO₅Si
• Molecular Weight: 393.555
• Mol file: 102679-24-3.mol

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

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

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-azetidinecarboxylic acid

There total 13 articles about (2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxylic acid 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: 97.0%

(2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxaldehyde (161806-13-9) → (2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxylic acid (102679-24-3)

Guidance literature:

With potassium permanganate; potassium carbonate; In tetrahydrofuran; water; for 15h; Ambient temperature;

DOI:10.1021/jo00110a035

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2S,3S)-3-<(R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-1-<(4-methoxyphenyl)methyl>-4-oxo-2-azetidinecarboxylic acid (102679-24-3)

Guidance literature:

Multi-step reaction with 4 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

4: 97 percent / KMnO₄, K₂CO₃ / H₂O; tetrahydrofuran / 15 h / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; potassium permanganate; sodium hydrogencarbonate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane; water; 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-azetidinecarboxylic acid (102679-24-3)

Guidance literature:

Multi-step reaction with 5 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

5: 97 percent / KMnO₄, K₂CO₃ / H₂O; tetrahydrofuran / 15 h / Ambient temperature

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

DOI:10.1021/jo00110a035

upstream raw materials:

tert-butyldimethylsilyl chloride

t-butyl (2S,3S)-3-<(R)-1-hydroxyethyl>-1-(4-methoxybenzyl)-4-oxo-2-azetidinecarboxylate

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

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

Downstream raw materials:

(3S,4R)-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-4-<(phenylthiocarbonyl)methyl>-2-azetidinone

3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<(phenylthio)carbonyl>methyl>azetidin-2-one

3-Chloro-benzoic acid (2R,3R)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-benzyl)-4-oxo-azetidin-2-yl ester

(3S,4S)-4-acetyl-3-<(R)-1-(t-butyldimethylsiloxy)ethyl>-1-(4-methoxybenzyl)-2-azetidinone