[(2R,3S)-2-((R)-3-Acetoxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: [(2R,3S)-2-((R)-3-Acetoxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester
• CAS No.: 135271-65-7
• Molecular Formula: C₄₅H₅₄NO₈PSi
• Molecular Weight: 795.985

Synonyms:[(2R,3S)-2-((R)-3-Acetoxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

Chemical Property of [(2R,3S)-2-((R)-3-Acetoxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

Chemical Property:

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Technology Process of [(2R,3S)-2-((R)-3-Acetoxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

There total 10 articles about [(2R,3S)-2-((R)-3-Acetoxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-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: 95.0%

triethylsilyl chloride (994-30-9) + [(2R,3S)-2-((R)-3-Acetoxy-1-methyl-2-oxo-propyl)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (112064-39-8) → [(2R,3S)-2-((R)-3-Acetoxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (135271-65-7)

Guidance literature:

With triethylamine; In dichloromethane; at 5 ℃; for 0.5h;

DOI:10.1248/cpb.39.663

Reference yield:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) → [(2R,3S)-2-((R)-3-Acetoxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (135271-65-7)

Guidance literature:

Multi-step reaction with 10 steps

1: 75 percent / Zn-powder / dimethylformamide / 12 h / 35 °C

2: 38 percent / BF₃*Et₂O / acetonitrile / 12 h / Ambient temperature

3: 96 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

4: 94 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

5: 59.7 percent / m-chloroperbenzoic acid, Na₂CO₃, MgSO₄ / CH₂Cl₂ / 48 h / Ambient temperature

6: 98 percent / Ti(OiPr)4 / 6 h / 32 °C

7: 1) DMSO, (CF₃CO)2O 2) Et₃N / 1) CH₂Cl₂, -70 deg C

9: 98 percent / conc. HCl / acetonitrile / 0.75 h / 5 °C

10: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 5 °C

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; boron trifluoride diethyl etherate; sodium carbonate; magnesium sulfate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; zinc; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.39.663

Reference yield:

(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(1-methyl-allyl)-azetidin-2-one (622410-46-2) → [(2R,3S)-2-((R)-3-Acetoxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (135271-65-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 38 percent / BF₃*Et₂O / acetonitrile / 12 h / Ambient temperature

2: 96 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

3: 94 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

4: 59.7 percent / m-chloroperbenzoic acid, Na₂CO₃, MgSO₄ / CH₂Cl₂ / 48 h / Ambient temperature

5: 98 percent / Ti(OiPr)4 / 6 h / 32 °C

6: 1) DMSO, (CF₃CO)2O 2) Et₃N / 1) CH₂Cl₂, -70 deg C

8: 98 percent / conc. HCl / acetonitrile / 0.75 h / 5 °C

9: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / 5 °C

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; boron trifluoride diethyl etherate; sodium carbonate; magnesium sulfate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1248/cpb.39.663

upstream raw materials:

triethylsilyl chloride

[(2R,3S)-2-((R)-3-Acetoxy-1-methyl-2-oxo-propyl)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(1-methyl-allyl)-azetidin-2-one

Downstream raw materials:

[(2R,3S)-2-((R)-3-Hydroxy-1-methyl-2-oxo-propyl)-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

Sodium (1S,5R,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-phenylthiomethylcarbapen-2-em-3-carboxylate

Sodium (1S,5R,6S)-2-(4-amino)phenylthiomethyl-6-<(R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate

p-Methoxybenzyl (1S,5R,6S)-2-Hydroxymethyl-1-methyl-6-<(R)-1-trinthylsilyloxyethyl>carbapen-2-em-3-carboxylate

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