(E)-3-Hydroxy-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(toluene-4-sulfonylsulfanyl)-azetidin-1-yl]-but-2-enoic acid benzhydryl ester

Base Information

• Chemical Name: (E)-3-Hydroxy-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(toluene-4-sulfonylsulfanyl)-azetidin-1-yl]-but-2-enoic acid benzhydryl ester
• CAS No.: 145918-85-0
• Molecular Formula: C₃₅H₃₂N₂O₈S₂
• Molecular Weight: 672.78
• Mol file: 145918-85-0.mol

Synonyms:(E)-3-Hydroxy-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(toluene-4-sulfonylsulfanyl)-azetidin-1-yl]-but-2-enoic acid benzhydryl ester

Chemical Property of (E)-3-Hydroxy-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(toluene-4-sulfonylsulfanyl)-azetidin-1-yl]-but-2-enoic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-Hydroxy-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(toluene-4-sulfonylsulfanyl)-azetidin-1-yl]-but-2-enoic acid benzhydryl ester

There total 1 articles about (E)-3-Hydroxy-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(toluene-4-sulfonylsulfanyl)-azetidin-1-yl]-but-2-enoic 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:

(R)-3-Methyl-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(toluene-4-sulfonylsulfanyl)-azetidin-1-yl]-but-3-enoic acid benzhydryl ester → (E)-3-Hydroxy-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(toluene-4-sulfonylsulfanyl)-azetidin-1-yl]-but-2-enoic acid benzhydryl ester (145918-85-0)

Guidance literature:

With dimethylsulfide; ozone; Yield given. Multistep reaction; 1.) MeOAc, -78 deg C;

DOI:10.1016/S0040-4039(00)92502-4

Reference yield: 86.0%

trifluoromethylsulfonic anhydride (358-23-6) + (E)-3-Hydroxy-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(toluene-4-sulfonylsulfanyl)-azetidin-1-yl]-but-2-enoic acid benzhydryl ester (145918-85-0) → (E)-2-[(3R,4R)-2-Oxo-3-(2-phenoxy-acetylamino)-4-(toluene-4-sulfonylsulfanyl)-azetidin-1-yl]-3-trifluoromethanesulfonyloxy-but-2-enoic acid benzhydryl ester (145836-27-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(00)92502-4

Reference yield:

(E)-3-Hydroxy-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(toluene-4-sulfonylsulfanyl)-azetidin-1-yl]-but-2-enoic acid benzhydryl ester (145918-85-0) → Diphenylmethyl (7S,6R)-7-(phenoxyacetamido)-3-(p-toluenesulfonyl)-3-cephem-4-carboxylate

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / iPr₂NEt / CH₂Cl₂ / -78 °C

2: 100 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

3: 61 percent / LiBr / various solvent(s) / 16 h / Ambient temperature

With triethylamine; N-ethyl-N,N-diisopropylamine; lithium bromide; In dichloromethane;

DOI:10.1016/S0040-4039(00)92502-4

Downstream raw materials:

(E)-2-[(3R,4R)-2-Oxo-3-(2-phenoxy-acetylamino)-4-(toluene-4-sulfonylsulfanyl)-azetidin-1-yl]-3-trifluoromethanesulfonyloxy-but-2-enoic acid benzhydryl ester

Diphenylmethyl 2-<(3R,4R)-4-<(p-toluenesulfonyl)thio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate