{(2R,3S)-2-[2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzyl ester

Base Information

• Chemical Name: {(2R,3S)-2-[2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzyl ester
• CAS No.: 73910-45-9
• Molecular Formula: C₄₅H₄₅N₂O₆P
• Molecular Weight: 740.836

Synonyms:

Chemical Property of {(2R,3S)-2-[2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-4-oxo-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 {(2R,3S)-2-[2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzyl ester

There total 13 articles about {(2R,3S)-2-[2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-4-oxo-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:

penicillin-V β-sulfoxide benzyl ester (4052-69-1) → {(2R,3S)-2-[2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid benzyl ester (73910-45-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 131 g / trimethylphosphite, molecular sieves / toluene / 2 h / Heating

2: 48 g / 0.5N HCl / methanol / 0.25 h / Heating

3: 1.) PCl₅, 2.) MeOH / 1.) r.t., 2 h, 2.) -40 deg C, r.t., 2 h

4: 1.) aq. NaHCO₃, 3.) molecular sieves (4A) / 1.) water, 2.) CH₂Cl₂, r.t., 15 min, 3.) 30 min

5: Et₃N / CH₂Cl₂ / -78 °C

6: 10 g / Et₃N / 2 h / Ambient temperature

7: Zn / CH₂Cl₂; acetic acid

8: 2.3 g / pyridine / 0.17 h

9: 14 g / 85percent mCPBA / CH₂Cl₂ / Ambient temperature

10: 1.) 30percent HClO₄, 2.) p-toluenesulfonic acid / 1.) acetone, water, r.t., 2.5 h, 2.) r.t., 1 h

11: 1.) O₃, 2.) Zn, acetic acid / 1.) CH₂Cl₂, ca. -78 deg C, 2.) -25 - -15 deg C

12: SOCl₂, pyridine / CH₂Cl₂

13: 1.58 g / CH₂Cl₂ / Heating

With pyridine; hydrogenchloride; methanol; thionyl chloride; perchloric acid; molecular sieve; 4 A molecular sieve; phosphorus pentachloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; phosphorous acid trimethyl ester; In methanol; dichloromethane; acetic acid; toluene;

DOI:10.1248/cpb.28.1563

Reference yield:

(R)-3-methyl-2-(2-phenoxymethyl-thiazole-4-carbonylamino)-but-3-enoic acid benzyl ester (68047-66-5) → {(2R,3S)-2-[2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid benzyl ester (73910-45-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) PCl₅, 2.) MeOH / 1.) r.t., 2 h, 2.) -40 deg C, r.t., 2 h

2: 1.) aq. NaHCO₃, 3.) molecular sieves (4A) / 1.) water, 2.) CH₂Cl₂, r.t., 15 min, 3.) 30 min

3: Et₃N / CH₂Cl₂ / -78 °C

4: 10 g / Et₃N / 2 h / Ambient temperature

5: Zn / CH₂Cl₂; acetic acid

6: 2.3 g / pyridine / 0.17 h

7: 14 g / 85percent mCPBA / CH₂Cl₂ / Ambient temperature

8: 1.) 30percent HClO₄, 2.) p-toluenesulfonic acid / 1.) acetone, water, r.t., 2.5 h, 2.) r.t., 1 h

9: 1.) O₃, 2.) Zn, acetic acid / 1.) CH₂Cl₂, ca. -78 deg C, 2.) -25 - -15 deg C

10: SOCl₂, pyridine / CH₂Cl₂

11: 1.58 g / CH₂Cl₂ / Heating

With pyridine; methanol; thionyl chloride; perchloric acid; 4 A molecular sieve; phosphorus pentachloride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In dichloromethane; acetic acid;

DOI:10.1248/cpb.28.1563

Reference yield:

(R)-3-Methyl-2-pent-4-en-(Z)-ylideneamino-but-3-enoic acid benzyl ester (73910-25-5) → {(2R,3S)-2-[2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid benzyl ester (73910-45-9)

Guidance literature:

Multi-step reaction with 9 steps

1: Et₃N / CH₂Cl₂ / -78 °C

2: 10 g / Et₃N / 2 h / Ambient temperature

3: Zn / CH₂Cl₂; acetic acid

4: 2.3 g / pyridine / 0.17 h

5: 14 g / 85percent mCPBA / CH₂Cl₂ / Ambient temperature

6: 1.) 30percent HClO₄, 2.) p-toluenesulfonic acid / 1.) acetone, water, r.t., 2.5 h, 2.) r.t., 1 h

7: 1.) O₃, 2.) Zn, acetic acid / 1.) CH₂Cl₂, ca. -78 deg C, 2.) -25 - -15 deg C

8: SOCl₂, pyridine / CH₂Cl₂

9: 1.58 g / CH₂Cl₂ / Heating

With pyridine; thionyl chloride; perchloric acid; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In dichloromethane; acetic acid;

DOI:10.1248/cpb.28.1563

upstream raw materials:

triphenylphosphine

penicillin-V β-sulfoxide benzyl ester

(R)-3-methyl-2-(2-phenoxymethyl-thiazole-4-carbonylamino)-but-3-enoic acid benzyl ester

(R)-3-Methyl-2-pent-4-en-(Z)-ylideneamino-but-3-enoic acid benzyl ester

Downstream raw materials:

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

benzyl 2-<3β-phenylacetylamino-4β-(4-chloroacetoxy-3-oxobutyl)-2-oxoazetidin-1-yl>-2-triphenylphosphorane-diylethanoate

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

(6R,7R)-3-(2-Chloro-acetoxymethyl)-7-{[1-(3,5-di-tert-butyl-4-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-7-methoxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

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