VPC-32104

Chemical Name: 3-[4-(Benzyloxy)phenyl]-2(S)-[9(Z)-octadecenamido]-3-oxopropyl dihydrogen phosphate
项目整合开发状态: Biological Testing
项目研究机构: University of Virginia (Originator)
合成路线:The protected serine derivative (I) is converted into the corresponding Weinreb amide (II) upon coupling with N,O-dimethyl hydroxylamine in the presence of CBr4/PPh3.Reaction of (II) with 4-(benzyloxy)phenylmagnesium iodide (III) affords ketone (IV).Subsequent acidic cleavage of the protecting groups of (IV) leads to the hydroxy amino ketone (V).This is then acylated by oleoyl chloride (VI) to furnish amide (VII).Phosphitylation of the primary alcohol group of (VII) with di-tert-butyl N,N-diisopropylphosphoramidite,followed by oxidation with H2O2 gives rise to phosphate ester (VIII).The tert-butyl groups of (VIII) are finally cleaved by means of trifluoroacetic acid in CH2Cl2 to provide the title compound.