diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-tert-butylceph-3-em-4-carboxylate

Base Information

• Chemical Name: diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-tert-butylceph-3-em-4-carboxylate
• CAS No.: 130516-11-9
• Molecular Formula: C₃₂H₃₂N₂O₅S
• Molecular Weight: 556.682
• Mol file: 130516-11-9.mol

Synonyms:diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-tert-butylceph-3-em-4-carboxylate

Chemical Property of diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-tert-butylceph-3-em-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-tert-butylceph-3-em-4-carboxylate

There total 9 articles about diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-tert-butylceph-3-em-4-carboxylate 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: 70.0%

lithium di-tertbutyl cuprate (23402-75-7) + diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<<(trifluoromethyl)sulfonyl>oxy>ceph-3-em-4-carboxylate (130516-07-3) → diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-tert-butylceph-3-em-4-carboxylate (130516-11-9)

Guidance literature:

With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃;

DOI:10.1016/S0040-4039(00)97404-5

Reference yield:

diphenylmethyl 3-hydroxy-2-<(3R,4R)-2-oxo-3-(phenoxyacetylamino)-4-(p-tolylsulfonylthio)-1-azetidinyl>-2-butenoate (57561-96-3) → diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-tert-butylceph-3-em-4-carboxylate (130516-11-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 86.5 percent / i-Pr₂NEt / CH₂Cl₂ / 1 h / -78 °C

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

3: 1.) CuI / 1.) THF, 15 min, 2.) THF, -78 deg C, 15 min

With copper(l) iodide; TEA; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo00096a045

Reference yield:

Diphenylmethyl 2-<(3R,4R)-<(p-toluenesulfonyl)thio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-3-<(methanesulfonyl)oxy>-2-butenoate (157584-71-9) → diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-tert-butylceph-3-em-4-carboxylate (130516-11-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / TEA / CH₂Cl₂ / 1 h / Ambient temperature

2: 1.) CuI / 1.) THF, 15 min, 2.) THF, -78 deg C, 15 min

With copper(l) iodide; TEA; In dichloromethane;

DOI:10.1021/jo00096a045

upstream raw materials:

tert-butylmagnesium bromide

diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<<(trifluoromethyl)sulfonyl>oxy>ceph-3-em-4-carboxylate

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

tert-butylmagnesium chloride