Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate

Base Information

• Chemical Name: Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate
• CAS No.: 143159-88-0
• Molecular Formula: C₃₅H₂₇N₃O₅S₃
• Molecular Weight: 665.814
• Mol file: 143159-88-0.mol

Synonyms:Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate

Chemical Property of Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate

There total 2 articles about Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate 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: 90.0%

Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-3-<(trifluoromethanesulfonyl)oxy>-2-butenoate → Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate (143159-88-0)

Guidance literature:

With TEA; In dichloromethane; for 0.75h; Ambient temperature;

DOI:10.1021/jo00096a045

Reference yield:

diphenylmethyl 2-<(3R,4R)-4-(2-benzothiazolyldithio)-2-oxo-3-(phenoxyacetylamino)-1-azetidinyl>-3-hydroxy-2-butenoate (57562-07-9) → Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate (143159-88-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / i-Pr₂NEt / CH₂Cl₂ / 1 h / -78 °C

2: 90 percent / TEA / CH₂Cl₂ / 0.75 h / Ambient temperature

With TEA; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo00096a045

Reference yield: 55.0%

Diphenylmethyl 2-<(3R,4R)-4-<(benzothiazol-2-yl)dithio>-3-(phenoxyacetamido)-2-oxoazetidin-1-yl>-2,3-butadienoate (143159-88-0) → diphenylmethyl (6R,7R)-3-methyl-7β-phenoxyacetamidoceph-3-em-4-carboxylate (10209-10-6) + diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<(Z)-1-propenyl>ceph-3-em-4-carboxylate (130516-13-1) + (6R,7R)-3-(Benzothiazol-2-ylsulfanyl)-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h; Yields of byproduct given;

DOI:10.1016/S0040-4039(00)92503-6

upstream raw materials:

diphenylmethyl 2-<(3R,4R)-4-(2-benzothiazolyldithio)-2-oxo-3-(phenoxyacetylamino)-1-azetidinyl>-3-hydroxy-2-butenoate

Downstream raw materials:

diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-<(Z)-1-propenyl>ceph-3-em-4-carboxylate

diphenylmethyl (6R,7S)-7-(phenoxyacetamido)-3-methylceph-2-em-4-carboxylate

diphenylmethyl (6R,7R)-3-methyl-7β-phenoxyacetamidoceph-3-em-4-carboxylate