[(2R,3S)-2-[(R)-5-tert-Butoxycarbonylamino-1-(2-hydroxy-acetyl)-pentyl]-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)-5-tert-Butoxycarbonylamino-1-(2-hydroxy-acetyl)-pentyl]-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester
• CAS No.: 220430-49-9
• Molecular Formula: C₅₆H₆₉N₂O₈PSi
• Molecular Weight: 957.232

Synonyms:[(2R,3S)-2-[(R)-5-tert-Butoxycarbonylamino-1-(2-hydroxy-acetyl)-pentyl]-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester

Chemical Property of [(2R,3S)-2-[(R)-5-tert-Butoxycarbonylamino-1-(2-hydroxy-acetyl)-pentyl]-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester

Chemical Property:

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Technology Process of [(2R,3S)-2-[(R)-5-tert-Butoxycarbonylamino-1-(2-hydroxy-acetyl)-pentyl]-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester

There total 12 articles about [(2R,3S)-2-[(R)-5-tert-Butoxycarbonylamino-1-(2-hydroxy-acetyl)-pentyl]-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: 57.0%

(3S,4R)-3-<(1R)-1-triethylsilyloxyethyl>-4-<(1R)-1-(4-tert-butoxycarbonylaminobutyl)-2-oxo-3-acetoxypropyl>-1-(2-diphenylmethoxycarbonyl-1-triphenylphosphoranylideneethyl)-2-azetidinone (220430-30-8) → [(2R,3S)-2-[(R)-5-tert-Butoxycarbonylamino-1-(2-hydroxy-acetyl)-pentyl]-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid benzhydryl ester (220430-49-9)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 5h;

DOI:10.3987/COM-98-8302

Reference yield:

Acetic acid (R)-7-azido-3-[(2R,3S)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-2-oxo-heptyl ester (220430-50-2) → [(2R,3S)-2-[(R)-5-tert-Butoxycarbonylamino-1-(2-hydroxy-acetyl)-pentyl]-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid benzhydryl ester (220430-49-9)

Guidance literature:

Multi-step reaction with 6 steps

1: imidazole / dimethylformamide / 0.5 h / 0 °C

2: 86 percent / H₂ / Pd/C / methanol / 0.25 h

3: 77 percent / toluene / 3 h / Heating

4: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.5 h / -40 °C

5: 2,6-lutidine, NaBr / tetrahydrofuran / 4 h / Ambient temperature

6: 57 percent / NaOMe / methanol / 5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; thionyl chloride; hydrogen; sodium methylate; sodium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.3987/COM-98-8302

Reference yield:

Acetic acid (S)-6-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-cyclohex-1-enylmethyl ester (220430-51-3) → [(2R,3S)-2-[(R)-5-tert-Butoxycarbonylamino-1-(2-hydroxy-acetyl)-pentyl]-4-oxo-3-((R)-1-triethylsilanyloxy-ethyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid benzhydryl ester (220430-49-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) O₃; 2.) dimethyl sulfide / 1.) CH₂Cl₂, CH₃OH, -78 deg C, 30 min

2: 71 percent / NaBH₄ / CH₂Cl₂; ethanol / 0.67 h / -78 °C

3: 82 percent / triphenylphosphine, HN₃, diethyl azodicarboxylate / tetrahydrofuran; toluene / 1 h / 0 °C

4: 82 percent / conc. HCl, acetic acid / acetonitrile / 2 h / 0 °C

5: imidazole / dimethylformamide / 0.5 h / 0 °C

6: 86 percent / H₂ / Pd/C / methanol / 0.25 h

7: 77 percent / toluene / 3 h / Heating

8: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.5 h / -40 °C

9: 2,6-lutidine, NaBr / tetrahydrofuran / 4 h / Ambient temperature

10: 57 percent / NaOMe / methanol / 5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; sodium tetrahydroborate; thionyl chloride; dimethylsulfide; tris-(2-chloro-ethyl)-amine; hydrogen; sodium methylate; ozone; acetic acid; triphenylphosphine; sodium bromide; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.3987/COM-98-8302

upstream raw materials:

(3S,4R)-3-<(1R)-1-triethylsilyloxyethyl>-4-<(1R)-1-(4-tert-butoxycarbonylaminobutyl)-2-oxo-3-acetoxypropyl>-1-(2-diphenylmethoxycarbonyl-1-triphenylphosphoranylideneethyl)-2-azetidinone

Acetic acid (R)-7-azido-3-[(2R,3S)-3-((R)-1-hydroxy-ethyl)-4-oxo-azetidin-2-yl]-2-oxo-heptyl ester

(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1S)-2-hydroxymethylcyclohex-2-enyl>-2-azetidinone

(S)-6-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-cyclohex-1-enecarboxylic acid ethyl ester

Downstream raw materials:

benzhydryl (1S,5R,6S)-1-(4-tert-butoxycarbonylaminobutyl)-2-hydroxymethyl-6-<(1R)-1-triethylsilyloxyethyl>carbapen-2-em-3-carboxylate

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

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