VPC-12249

Chemical Name: 3-[4-(Benzyloxy)phenyl]-2(S)-[9(Z)-octadecenamido]propyl 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:N-Boc-O-benzyltyrosine (I) was converted to the aminoalcohol derivative (III) via conversion to the mixed anhydride (II) with isobutyl chloroformate and subsequent reduction with NaBH4.Acid cleavage of the N-Boc protecting group of (III) gave the free amine (IV),which was acylated with oleoyl chloride (V) to afford amide (VI).Phosphitylation of (VI) with N,N-diisopropyl di-tert-butyl phosphoroamidite in the presence of tetrazole,followed by oxidation of the intermediate phosphite with hydrogen peroxide,furnished the phosphate (VII).The tert-butyl phosphate ester groups of (VII) were finally cleaved by treatment with trifluoroacetic acid.