(6R,7R)-3-Methyl-8-oxo-7-phenylacetylamino-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (6R,7R)-3-Methyl-8-oxo-7-phenylacetylamino-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 76231-32-8
• Molecular Formula: C₂₉H₂₆N₂O₅
• Molecular Weight: 482.536

Synonyms:(6R,7R)-3-Methyl-8-oxo-7-phenylacetylamino-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property of (6R,7R)-3-Methyl-8-oxo-7-phenylacetylamino-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property:

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Technology Process of (6R,7R)-3-Methyl-8-oxo-7-phenylacetylamino-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 7 articles about (6R,7R)-3-Methyl-8-oxo-7-phenylacetylamino-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic 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: 49.0%

(Z)-4-Hydroxy-3-methyl-2-((3S,4R)-2-oxo-3-phenylacetylamino-4-p-tolyldisulfanyl-azetidin-1-yl)-but-2-enoic acid benzhydryl ester (76173-01-8) → (6R,7R)-3-Methyl-8-oxo-7-phenylacetylamino-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (76231-32-8)

Guidance literature:

With mercury(II) trifluoroacetate;

DOI:10.1021/jo00317a043

Reference yield: 30.0%

(Z)-2-{(2R,3S)-2-[(2R,3S)-1-((Z)-1-Benzhydryloxycarbonyl-3-hydroxy-2-methyl-propenyl)-4-oxo-3-phenylacetylamino-azetidin-2-yldisulfanyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-4-hydroxy-3-methyl-but-2-enoic acid benzhydryl ester (76173-00-7) → (6R,7R)-3-Methyl-8-oxo-7-phenylacetylamino-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (76231-32-8)

Guidance literature:

With mercury(II) trifluoroacetate; In acetonitrile; at 25 ℃; for 0.5h;

DOI:10.1021/jo00317a043

Reference yield:

7-amino-3-methyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (116404-19-4) + phenylacetyl chloride (103-80-0) → 3-methyl-8-oxo-7-(2-phenyl-acetylamino)-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (63881-86-7,76231-32-8,83349-18-2)

Guidance literature:

With hydrogenchloride; sodium hydrogencarbonate; triethylamine; In dichloromethane; water;

upstream raw materials:

7-amino-3-methyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

phenylacetyl chloride

(Z)-4-Hydroxy-3-methyl-2-((3S,4R)-2-oxo-3-phenylacetylamino-4-p-tolyldisulfanyl-azetidin-1-yl)-but-2-enoic acid benzhydryl ester

(Z)-2-{(2R,3S)-2-[(2R,3S)-1-((Z)-1-Benzhydryloxycarbonyl-3-hydroxy-2-methyl-propenyl)-4-oxo-3-phenylacetylamino-azetidin-2-yldisulfanyl]-4-oxo-3-phenylacetylamino-azetidin-1-yl}-4-hydroxy-3-methyl-but-2-enoic acid benzhydryl ester

Downstream raw materials:

diphenylmethyl 7β-(phenylacetamido)-7α-methoxy-3-methyl-1-oxadethia-3-cephem-4-carboxylate

7β-(phenylacetamido)-7α-methoxy-3-methyl-1-oxadethia-3-cephem-4-carboxylic acid

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