[(2R,3S)-3-((R)-1-Hydroxy-ethyl)-2-((1R,3S)-3-hydroxy-2-oxo-cyclohexyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester

Base Information

• Chemical Name: [(2R,3S)-3-((R)-1-Hydroxy-ethyl)-2-((1R,3S)-3-hydroxy-2-oxo-cyclohexyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester
• CAS No.: 220430-48-8
• Molecular Formula: C₄₄H₄₂NO₆P
• Molecular Weight: 711.794

Synonyms:

Chemical Property of [(2R,3S)-3-((R)-1-Hydroxy-ethyl)-2-((1R,3S)-3-hydroxy-2-oxo-cyclohexyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3S)-3-((R)-1-Hydroxy-ethyl)-2-((1R,3S)-3-hydroxy-2-oxo-cyclohexyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester

There total 11 articles about [(2R,3S)-3-((R)-1-Hydroxy-ethyl)-2-((1R,3S)-3-hydroxy-2-oxo-cyclohexyl)-4-oxo-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:

(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R,3S)-3-triethylsilyloxy-2-oxocyclohexyl>-1-(diphenylmethoxycarbonyl-triphenylphosphoranylidenemethyl)-2-azetidinone (220430-37-5) → [(2R,3S)-3-((R)-1-Hydroxy-ethyl)-2-((1R,3S)-3-hydroxy-2-oxo-cyclohexyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid benzhydryl ester (220430-48-8)

Guidance literature:

With hydrogenchloride; acetic acid; In acetonitrile; at 0 ℃; for 1h; Yield given;

DOI:10.3987/COM-98-8302

Reference yield:

6-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester (28469-52-5) → [(2R,3S)-3-((R)-1-Hydroxy-ethyl)-2-((1R,3S)-3-hydroxy-2-oxo-cyclohexyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid benzhydryl ester (220430-48-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 82 percent / NBS, dimethyl sulfide / CH₂Cl₂ / 2.5 h / Ambient temperature

2: 30 percent / zinc dust / tetrahydrofuran / 1 h / 40 °C

3: 60 percent / DIBAL-H / toluene; methanol / -78 - 0 °C

4: 85 percent / tri-n-butylphosphine / CH₂Cl₂ / 1 h / -78 °C

5: 50 percent / 30 percent H₂O₂ / pyridine; H₂O / 0.5 h / Ambient temperature

6: 83 percent / O₃; dimethyl sulfide / CH₂Cl₂; methanol / 0.17 h / -78 °C

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

8: 88 percent / toluene / 3 h / Heating

9: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.5 h / -40 °C

10: 2,6-lutidine, NaBr / tetrahydrofuran / 4 h / Ambient temperature

11: conc. HCl, acetic acid / acetonitrile / 1 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; N-Bromosuccinimide; thionyl chloride; dimethylsulfide; tributylphosphine; dihydrogen peroxide; diisobutylaluminium hydride; ozone; acetic acid; sodium bromide; zinc; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.3987/COM-98-8302

Reference yield:

6-bromocyclohex-1-enecarboxylic acid ethyl ester (119105-31-6) → [(2R,3S)-3-((R)-1-Hydroxy-ethyl)-2-((1R,3S)-3-hydroxy-2-oxo-cyclohexyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid benzhydryl ester (220430-48-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 30 percent / zinc dust / tetrahydrofuran / 1 h / 40 °C

2: 60 percent / DIBAL-H / toluene; methanol / -78 - 0 °C

3: 85 percent / tri-n-butylphosphine / CH₂Cl₂ / 1 h / -78 °C

4: 50 percent / 30 percent H₂O₂ / pyridine; H₂O / 0.5 h / Ambient temperature

5: 83 percent / O₃; dimethyl sulfide / CH₂Cl₂; methanol / 0.17 h / -78 °C

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

7: 88 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: conc. HCl, acetic acid / acetonitrile / 1 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; thionyl chloride; dimethylsulfide; tributylphosphine; dihydrogen peroxide; diisobutylaluminium hydride; ozone; acetic acid; sodium bromide; zinc; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.3987/COM-98-8302

upstream raw materials:

(3S,4R)-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>-4-<(1R,3S)-3-triethylsilyloxy-2-oxocyclohexyl>-1-(diphenylmethoxycarbonyl-triphenylphosphoranylidenemethyl)-2-azetidinone

6-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester

6-bromocyclohex-1-enecarboxylic acid ethyl ester

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

Downstream raw materials:

benzhydryl (4S,8S,9R,10S)-4-hydroxy-10-<(1R)-1-hydroxyethyl>-11-oxo-1-azatricyclo-<7.2.0.0^3,8>undec-2-ene-2-carboxylate

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