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- W2076557110 abstract "A simple synthesis of optically active phosphorylated oxazoles 8, 10, 11, and 12 containing amino acid residues from 2H-azirine-phosphine oxides 1 or -phosphonates 6 is described. Ring-opening reaction of 2H-azirines derived from phosphine oxides 1 and phosphonates 6 with N-protected amino acids 2 gives functionalized phosphorylated ketamides 3 and 7. Cyclization of ketamides 3 and 7 with triphenylphosphine and hexachloroethane in the presence of triethylamine leads to the formation of racemic and optically active phosphorylated oxazoles containing N-protected amino acid residues 8 and 10. Deprotection of these oxazoles gives aminoalkyl oxazoles 11 and 12. 2H-Azirines 1 and 6 also react with N-protected peptides 13 and give functionalized ketamides 14 and 15, ring closure of which leads to the formation of phosphorylated oxazoles containing peptide residues 16 and 17." @default.
- W2076557110 created "2016-06-24" @default.
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- W2076557110 date "2002-11-01" @default.
- W2076557110 modified "2023-10-16" @default.
- W2076557110 title "Synthesis of optically active oxazoles from phosphorylated 2H-azirines and N-protected amino acids or peptides" @default.
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- W2076557110 doi "https://doi.org/10.1016/s0957-4166(02)00686-9" @default.
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