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

Base Information

• Chemical Name: [(2R,3S)-2-{(R)-3-Hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-propyl}-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester
• CAS No.: 220430-45-5
• Molecular Formula: C₅₇H₆₄NO₈PSi
• Molecular Weight: 950.196

Synonyms:[(2R,3S)-2-{(R)-3-Hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-propyl}-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester

Chemical Property of [(2R,3S)-2-{(R)-3-Hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-propyl}-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester

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Technology Process of [(2R,3S)-2-{(R)-3-Hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-propyl}-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester

There total 15 articles about [(2R,3S)-2-{(R)-3-Hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-propyl}-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl 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: 59.0%

(3S,4R)-3-<(1R)-1-triethylsilyloxyethyl>-4-<(1S)-1-(2-p-methoxybenzyloxyethyl)-2-oxo-3-acetoxypropyl>-1-(diphenylmethoxycarbonyl-triphenylphosphoranylidenemethyl)-2-azetidinone (220430-16-0) → [(2R,3S)-2-{(R)-3-Hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-propyl}-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid benzhydryl ester (220430-45-5)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 3h;

DOI:10.3987/COM-98-8302

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → [(2R,3S)-2-{(R)-3-Hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-propyl}-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid benzhydryl ester (220430-45-5)

Guidance literature:

Multi-step reaction with 14 steps

1: NaH / dimethylformamide / 1 h / Ambient temperature

2: O₃; dimethyl sulfide / CH₂Cl₂; methanol / 1.5 h / -78 °C

3: 60 percent / 3-quinuclidinol / neat (no solvent) / 48 h / Ambient temperature

4: 76 percent / NBS, dimethylsulfide / CH₂Cl₂; toluene / 15 h / Ambient temperature

5: 92 percent / zinc dust / dimethylformamide / 2 h / Ambient temperature

6: DIBAL-H / toluene; methanol / -78 - 0 °C

7: triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

8: conc. HCl, acetic acid / acetonitrile / 0.5 h / 0 °C

9: imidazole / dimethylformamide / 0.33 h / 0 °C

10: 1.) O₃; 2.) dimethylsulfide / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 40 min

11: 87 percent / 4 Angstroem molecular sieves / toluene / 3 h / Heating

12: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.5 h / -40 °C

13: 2,6-lutidine, NaBr / tetrahydrofuran / 1 h / Ambient temperature

14: 59 percent / NaOMe / methanol / 3 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; N-Bromosuccinimide; thionyl chloride; dimethylsulfide; 4 A molecular sieve; sodium methylate; sodium hydride; diisobutylaluminium hydride; ozone; acetic acid; triethylamine; 3-quinuclidinol; sodium bromide; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.3987/COM-98-8302

Reference yield:

3-(p-methoxybenzyloxy)propanal (128461-65-4) → [(2R,3S)-2-{(R)-3-Hydroxy-1-[2-(4-methoxy-benzyloxy)-ethyl]-2-oxo-propyl}-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid benzhydryl ester (220430-45-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 60 percent / 3-quinuclidinol / neat (no solvent) / 48 h / Ambient temperature

2: 76 percent / NBS, dimethylsulfide / CH₂Cl₂; toluene / 15 h / Ambient temperature

3: 92 percent / zinc dust / dimethylformamide / 2 h / Ambient temperature

4: DIBAL-H / toluene; methanol / -78 - 0 °C

5: triethylamine / CH₂Cl₂ / 0.25 h / 0 °C

6: conc. HCl, acetic acid / acetonitrile / 0.5 h / 0 °C

7: imidazole / dimethylformamide / 0.33 h / 0 °C

8: 1.) O₃; 2.) dimethylsulfide / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 40 min

9: 87 percent / 4 Angstroem molecular sieves / toluene / 3 h / Heating

10: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.5 h / -40 °C

11: 2,6-lutidine, NaBr / tetrahydrofuran / 1 h / Ambient temperature

12: 59 percent / NaOMe / methanol / 3 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; N-Bromosuccinimide; thionyl chloride; dimethylsulfide; 4 A molecular sieve; sodium methylate; diisobutylaluminium hydride; ozone; acetic acid; triethylamine; 3-quinuclidinol; sodium bromide; zinc; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.3987/COM-98-8302

upstream raw materials:

(3S,4R)-3-<(1R)-1-triethylsilyloxyethyl>-4-<(1S)-1-(2-p-methoxybenzyloxyethyl)-2-oxo-3-acetoxypropyl>-1-(diphenylmethoxycarbonyl-triphenylphosphoranylidenemethyl)-2-azetidinone

p-Methoxybenzyl bromide

3-(p-methoxybenzyloxy)propanal

4-Methoxybenzyl alcohol

Downstream raw materials:

benzhydryl (1S,5R,6S)-1-(2-p-methoxybenzyloxyethyl)-2-hydroxymethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

benzhydryl (1S,5R,6S)-1-(2-p-methoxybenzyloxyethyl)-2-(1,3,4-thiadiazol-2-yl)thiomethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

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