2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-buta-2,3-dienoic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: 2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-buta-2,3-dienoic acid 4-methoxy-benzyl ester
• CAS No.: 139472-60-9
• Molecular Formula: C₂₉H₂₆N₂O₇S₂
• Molecular Weight: 578.667
• Mol file: 139472-60-9.mol

Synonyms:2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-buta-2,3-dienoic acid 4-methoxy-benzyl ester

Chemical Property of 2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-buta-2,3-dienoic acid 4-methoxy-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-buta-2,3-dienoic acid 4-methoxy-benzyl ester

There total 9 articles about 2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-buta-2,3-dienoic acid 4-methoxy-benzyl 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: 78.0%

p-methoxybenzyl (E)-3,4-dichloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-2-butenoate (168418-31-3) → 2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-buta-2,3-dienoic acid 4-methoxy-benzyl ester (139472-60-9)

Guidance literature:

With [2,2]bipyridinyl; benzyltributyltin; copper(l) chloride; In various solvent(s); Ambient temperature;

DOI:10.1055/s-1999-2735

Reference yield:

(E)-2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-4-chloro-3-hydroxy-but-2-enoic acid 4-methoxy-benzyl ester (131857-34-6) → 2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-buta-2,3-dienoic acid 4-methoxy-benzyl ester (139472-60-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / Et₃N / CH₂Cl₂ / 1 h / -78 °C

2: 83 percent / LiCl, AlCl₃, N-methylpyrrolidine / 4 h / Ambient temperature

3: 2 percent Chromat_. / TiCl₄, Al, NMP / CH₂Cl₂ / 6.5 h / Ambient temperature

With 1-Methylpyrrolidine; 1-methyl-pyrrolidin-2-one; aluminium trichloride; titanium tetrachloride; triethylamine; aluminium; lithium chloride; In dichloromethane;

DOI:10.1021/jo970051n

Reference yield:

p-methoxybenzyl (E)-3,4-dichloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-2-butenoate (168418-31-3) → 3-methylene-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxybenzyl ester (139371-98-5) + 2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-buta-2,3-dienoic acid 4-methoxy-benzyl ester (139472-60-9) + 3-chloro-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxybenzyl ester (139501-51-2) + p-methoxybenzyl (Z)-3-chloro-2-{2-oxo-3-(phenylacetamido)-4-[(phenylsulfonyl)thio]azetidin-1-yl}-2-butenoate

Guidance literature:

With 1-methyl-pyrrolidin-2-one; aluminium trichloride; aluminium; for 7.6h; Further byproducts given; Ambient temperature;

DOI:10.1021/jo970051n

upstream raw materials:

p-methoxybenzyl (E)-3,4-dichloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-2-butenoate

p-methoxybenzyl (E)-3-chloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-4-<<(trifluoromethyl)sulfonyl>oxy>-2-butenoate

p-methoxybenzyl (Z)-3-chloro-4-{[(p-methylphenyl)sulfonyl]oxy}-2-{2-oxo-3-(phenylacetamido)-4-[(phenylsulfonyl)thio]azetidin-1-yl}-2-butenoate

(E)-2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-4-chloro-3-(toluene-4-sulfonyloxy)-but-2-enoic acid 4-methoxy-benzyl ester

Downstream raw materials:

3-methylene-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxybenzyl ester

3-chloro-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxybenzyl ester

(6R,7R)-3-(2-Methyl-propenyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

(7R,8R)-7-phenylacetamido-3-[(Z)-propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester