(S)-2-Benzyloxycarbonylamino-4-((S)-3-hydroxy-2-oxo-azetidin-3-yl)-butyric acid

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-4-((S)-3-hydroxy-2-oxo-azetidin-3-yl)-butyric acid
• CAS No.: 137627-23-7
• Molecular Formula: C₁₅H₁₈N₂O₆
• Molecular Weight: 322.318
• Mol file: 137627-23-7.mol

Synonyms:(S)-2-Benzyloxycarbonylamino-4-((S)-3-hydroxy-2-oxo-azetidin-3-yl)-butyric acid

Chemical Property of (S)-2-Benzyloxycarbonylamino-4-((S)-3-hydroxy-2-oxo-azetidin-3-yl)-butyric acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyloxycarbonylamino-4-((S)-3-hydroxy-2-oxo-azetidin-3-yl)-butyric acid

There total 4 articles about (S)-2-Benzyloxycarbonylamino-4-((S)-3-hydroxy-2-oxo-azetidin-3-yl)-butyric 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: 75.0%

(3S,3'S)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone (137627-22-6) → (S)-2-Benzyloxycarbonylamino-4-((S)-3-hydroxy-2-oxo-azetidin-3-yl)-butyric acid (137627-23-7)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 25 ℃; for 0.5h;

DOI:10.1021/jo00027a024

Reference yield:

(3RS,3'E,5'R)-1-(tert-butyldimethylsilyl)-3-<5'-(methylthio)hex-3'-enyl>-3-<(trimethylsilyl)oxy>-2-oxoazetidine (137627-18-0) → (S)-2-Benzyloxycarbonylamino-4-((S)-3-hydroxy-2-oxo-azetidin-3-yl)-butyric acid (137627-23-7)

Guidance literature:

Multi-step reaction with 4 steps

2: 1.) ozone, Me₂S, 2.) PCC, NaOAC, 4 Angstroem molecular sieves / 1.) MeOH, -78 deg C; 25 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 3 h

3: 84 percent / n-Bu₄NF, glacial acetic acid / tetrahydrofuran / 1 h

4: 75 percent / 1 N aq. NaOH / tetrahydrofuran; H₂O / 0.5 h / 25 °C

With sodium hydroxide; dimethylsulfide; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium acetate; ozone; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; water;

DOI:10.1021/jo00027a024

Reference yield:

(3RS,3'S,4'E)-1-(tert-butyldimethylsilyl)-3-<3'-<(benzyloxycarbonyl)amino>hex-4'-enyl>-3-hydroxy-2-oxoazetidine (137627-20-4,137627-26-0) → (S)-2-Benzyloxycarbonylamino-4-((S)-3-hydroxy-2-oxo-azetidin-3-yl)-butyric acid (137627-23-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) ozone, Me₂S, 2.) PCC, NaOAC, 4 Angstroem molecular sieves / 1.) MeOH, -78 deg C; 25 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 3 h

2: 84 percent / n-Bu₄NF, glacial acetic acid / tetrahydrofuran / 1 h

3: 75 percent / 1 N aq. NaOH / tetrahydrofuran; H₂O / 0.5 h / 25 °C

With sodium hydroxide; dimethylsulfide; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium acetate; ozone; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; water;

DOI:10.1021/jo00027a024

upstream raw materials:

(3S,3'S)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone

(3RS,3'E,5'R)-1-(tert-butyldimethylsilyl)-3-<5'-(methylthio)hex-3'-enyl>-3-<(trimethylsilyl)oxy>-2-oxoazetidine

(3RS,3'S,4'E)-1-(tert-butyldimethylsilyl)-3-<3'-<(benzyloxycarbonyl)amino>hex-4'-enyl>-3-hydroxy-2-oxoazetidine

(3S,3'S)-1-(tert-butyldimethylsilyl)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone

Downstream raw materials:

(3S,3'S)-3-(3'-amino-3'-carboxypropyl)-3-hydroxy-2-azetidinone