4-NITROBENZYL-(1R,5R,6S)-6-[(1R)-1-HYDROXYETHYL]-2-[(DIPHENYLPHOSPHONO)OXY]-1-METHYLCARBAPEN-2-EM-3-CARBOXYLIC ACID

4-NITROBENZYL-(1R,5R,6S)-6-[(1R)-1-HYDROXYETHYL]-2-[(DIPHENYLPHOSPHONO)OXY]-1-METHYLCARBAPEN-2-EM-3-CARBOXYLIC ACID

Product name:(4r,5s,6s)-3-(diphenyloxy)phosphoryloxy-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate CAS:90776-59-3 MF:C29H27N2O10P MW:594.51 Assay: 99%min Appearance: white crystalline powder Application: Pharmaceutical intermedicate Place of origin:Xinxiang...

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Product Details

Product name:(4r,5s,6s)-3-(diphenyloxy)phosphoryloxy-6-[(1r)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3,2,0]hept-2-ene-2-carboxylate

CAS:90776-59-3

MF:C29H27N2O10P

MW:594.51

Assay: 99%min

Appearance: white crystalline powder

Application: Pharmaceutical intermedicate

Place of origin:Xinxiang

Synthetic method:

  The condensation of (3R,4R)-4-acetoxy-3-[1(R)-(tert-butyldimethylsilylioxy)ethyl)azetidin-2-one (I) with benzyl 2-bromopropionate (II) by means of diethylaluminum chloride in hexane - THF gives the isomeric mixture (III), (IIIa), which is separated by column chrornatography and the correct isomer (III) is treated with tert-butyldimethylsilyl chloride to yield the silylated azetidine (IV). The reductive debenzylation of (IV) with H2 over Pd/C in methanol affords the protected free acid (V), which is condensed with magnesium 4-nitrobenzylmalonate (VI) by means of carbonyldiimidazole (CDI) in hot acetonitrile to give the protected ketoester (VII). Partial hydrolysis of (VII) with HCl in methanol affords the free ketoester (VIII), which is treated with p-toluenesulfonylazide in acetonitrile yielding the diazo compound (IX). The cyclization of (IX) by means of rhodium acetate in refluxing toluene gives 6alpha-[1(R)-hydroxyethyl)-1beta-methyl-2-oxo-1-dethia-1-carba-2-penem-3-car boxylic acid 4-nitrobenzyl ester (X), which is condensed with diphenyl chlorophosphate (XI) by means of diisopropylethylamine in acetonitrile, yielding the enol ester (XII).





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