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

Base Information

• Chemical Name: (3S,3'S)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone
• CAS No.: 137627-22-6
• Molecular Formula: C₁₅H₁₆N₂O₅
• Molecular Weight: 304.302
• Mol file: 137627-22-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (3S,3'S)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone 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: 84.0%

(3S,3'S)-1-(tert-butyldimethylsilyl)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone (137627-21-5) → (3S,3'S)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone (137627-22-6)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 1h;

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) → (3S,3'S)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone (137627-22-6)

Guidance literature:

Multi-step reaction with 3 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

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

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) → (3S,3'S)-3-<3'-<(benzyloxycarbonyl)amino>-3'-carboxypropyl>-3-hydroxy-2-oxoazetidine δ-lactone (137627-22-6)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1021/jo00027a024

upstream raw materials:

(3S,3'S)-1-(tert-butyldimethylsilyl)-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

Downstream raw materials:

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

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