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

Base Information

• Chemical Name: (3S,4S)-3-<(R)-1-(Formyloxy)ethyl>-1-<(4-methoxyphenyl)methyl>-4-<(phenylthio)methyl>-2-azetidinone
• CAS No.: 161806-11-7
• Molecular Formula: C₂₁H₂₃NO₄S
• Molecular Weight: 385.484
• Mol file: 161806-11-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (3S,4S)-3-<(R)-1-(Formyloxy)ethyl>-1-<(4-methoxyphenyl)methyl>-4-<(phenylthio)methyl>-2-azetidinone 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: 79.0%

formic acid (64-18-6) + (3S,4S)-3-<(S)-1-Hydroxyethyl>-1-<(4-methoxyphenyl)methyl>-4-<(phenylthio)methyl>-2-azetidinone (161806-10-6) → (3S,4S)-3-<(R)-1-(Formyloxy)ethyl>-1-<(4-methoxyphenyl)methyl>-4-<(phenylthio)methyl>-2-azetidinone (161806-11-7)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/jo00110a035

Reference yield:

(3S,4S)-3-<(S)-1-Hydroxyethyl>-1-<(4-methoxyphenyl)methyl>-4--2-azetidinone (153924-18-6) → (3S,4S)-3-<(R)-1-(Formyloxy)ethyl>-1-<(4-methoxyphenyl)methyl>-4-<(phenylthio)methyl>-2-azetidinone (161806-11-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / Bu₃SnH, AIBN / toluene / 14 h / Heating

2: 79 percent / diisopropyl azodicarboxylate, PPh₃ / tetrahydrofuran / 2 h / Ambient temperature

With 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; triphenylphosphine; In tetrahydrofuran; toluene;

DOI:10.1021/jo00110a035

Reference yield:

(3SR,4SR)-3-<(S)-1-Acetoxyethyl>-1-<(4-methoxyphenyl)methyl>-4--2-azetidinone → (3S,4S)-3-<(R)-1-(Formyloxy)ethyl>-1-<(4-methoxyphenyl)methyl>-4-<(phenylthio)methyl>-2-azetidinone (161806-11-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 56 percent / 0.1 N aq. NaOH / pyridine / Ambient temperature

2: 97 percent / Bu₃SnH, AIBN / toluene / 14 h / Heating

3: 79 percent / diisopropyl azodicarboxylate, PPh₃ / tetrahydrofuran / 2 h / Ambient temperature

With sodium hydroxide; 2,2'-azobis(isobutyronitrile); di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; triphenylphosphine; In tetrahydrofuran; pyridine; toluene;

DOI:10.1021/jo00110a035

upstream raw materials:

formic acid

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

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

Downstream raw materials:

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

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

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

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