[(3S,4R)-2-Oxo-4-((E)-3-oxo-but-1-enyl)-3-phenylacetylamino-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzyl ester

Base Information

• Chemical Name: [(3S,4R)-2-Oxo-4-((E)-3-oxo-but-1-enyl)-3-phenylacetylamino-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzyl ester
• CAS No.: 75460-15-0
• Molecular Formula: C₄₂H₃₇N₂O₅P
• Molecular Weight: 680.74

Synonyms:[(3S,4R)-2-Oxo-4-((E)-3-oxo-but-1-enyl)-3-phenylacetylamino-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzyl ester

Chemical Property of [(3S,4R)-2-Oxo-4-((E)-3-oxo-but-1-enyl)-3-phenylacetylamino-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(3S,4R)-2-Oxo-4-((E)-3-oxo-but-1-enyl)-3-phenylacetylamino-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzyl ester

There total 9 articles about [(3S,4R)-2-Oxo-4-((E)-3-oxo-but-1-enyl)-3-phenylacetylamino-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzyl ester 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:

(R)-3-Methyl-2-[(E)-3-phenyl-prop-2-en-(Z)-ylideneamino]-but-3-enoic acid benzyl ester (75460-09-2) → [(3S,4R)-2-Oxo-4-((E)-3-oxo-but-1-enyl)-3-phenylacetylamino-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid benzyl ester (75460-15-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) Et₃N, 2.) Et₃N / 1.) -30 -10 deg C, 1 h, 2.) r.t., 1 h

2: 38 g / Zn / CH₂Cl₂; acetic acid / 1 h / Ambient temperature

3: 21 g / pyridine / CH₂Cl₂ / 1 h / Ambient temperature; -40 deg C - room temp.

4: 1.) O₃, 2.) Zn / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, acetic acid, -10 deg C, 50 min

5: 4.23 g / CH₂Cl₂ / 1.) r.t., overnight, 2.) reflux, 40 min

6: SOCl₂, pyridine / CH₂Cl₂ / 0.33 h

7: 2.39 g / CH₂Cl₂ / 1.5 h / Heating

With pyridine; thionyl chloride; ozone; triethylamine; zinc; In dichloromethane; acetic acid;

DOI:10.1248/cpb.28.1578

Reference yield:

(-)-isodehydrovaline benzyl ester hydrochloride (75520-53-5) → [(3S,4R)-2-Oxo-4-((E)-3-oxo-but-1-enyl)-3-phenylacetylamino-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid benzyl ester (75460-15-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) aq. NaHCO₃, 2.) molecular sieves (4A) / 1.) water, 2.) CH₂Cl₂, reflux, 2 h

2: 1.) Et₃N, 2.) Et₃N / 1.) -30 -10 deg C, 1 h, 2.) r.t., 1 h

3: 38 g / Zn / CH₂Cl₂; acetic acid / 1 h / Ambient temperature

4: 21 g / pyridine / CH₂Cl₂ / 1 h / Ambient temperature; -40 deg C - room temp.

5: 1.) O₃, 2.) Zn / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, acetic acid, -10 deg C, 50 min

6: 4.23 g / CH₂Cl₂ / 1.) r.t., overnight, 2.) reflux, 40 min

7: SOCl₂, pyridine / CH₂Cl₂ / 0.33 h

8: 2.39 g / CH₂Cl₂ / 1.5 h / Heating

With pyridine; thionyl chloride; 4 A molecular sieve; sodium hydrogencarbonate; ozone; triethylamine; zinc; In dichloromethane; acetic acid;

DOI:10.1248/cpb.28.1578

Reference yield:

2-[(3S,4R)-3-Amino-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-methyl-but-2-enoic acid benzyl ester (75460-21-8) → [(3S,4R)-2-Oxo-4-((E)-3-oxo-but-1-enyl)-3-phenylacetylamino-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid benzyl ester (75460-15-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 21 g / pyridine / CH₂Cl₂ / 1 h / Ambient temperature; -40 deg C - room temp.

2: 1.) O₃, 2.) Zn / 1.) CH₂Cl₂, -78 deg C, 2.) CH₂Cl₂, acetic acid, -10 deg C, 50 min

3: 4.23 g / CH₂Cl₂ / 1.) r.t., overnight, 2.) reflux, 40 min

4: SOCl₂, pyridine / CH₂Cl₂ / 0.33 h

5: 2.39 g / CH₂Cl₂ / 1.5 h / Heating

With pyridine; thionyl chloride; ozone; zinc; In dichloromethane;

DOI:10.1248/cpb.28.1578

upstream raw materials:

triphenylphosphine

(R)-3-Methyl-2-[(E)-3-phenyl-prop-2-en-(Z)-ylideneamino]-but-3-enoic acid benzyl ester

2-[(3S,4R)-3-Amino-2-oxo-4-((E)-styryl)-azetidin-1-yl]-3-methyl-but-2-enoic acid benzyl ester

((2S,3S)-2-Formyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-hydroxy-acetic acid benzyl ester

Downstream raw materials:

benzyl 7β-amino-3-methyl-1,2-dehydro-1-carba-1-dethia-3-cephem-4-carboxylate

7β-<(2R)-2-phenyl-2-amino>acetylamino-3-methyl-1,2-dehydro-1-carba-1-dethia-3-cephem-4-carboxylic acid

benzyl 7β-phenylacetylamino-3-methyl-1,2-dehydro-1-carba-1-dethia-3-cephem-4-carboxylate

benzyl 7β-phenylacetylamino-3-methyl-1-carba-1-dethia-3-cephem-4-carboxylate

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