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Matches in SemOpenAlex for { <https://semopenalex.org/work/W2002249662> ?p ?o ?g. }

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• W2002249662 abstract "A practical 4-step synthesis of fibrinogen receptor antagonist MK-383, N-(n-butanesulfonyl)-O-(4-(4-piperidinyl)-butyl)-(S)-tyrosine, is accomplished in 48% overall yield from (S)-tyrosine. Highlights include: (1) the dual use of 4-picoline as a masked form of piperidine, and as a nucleophile precursor for a 3-carbon homologation with 3-bromo-1-chloropropane; (2) the use of trimethylsilyl groups for temporary protection of phenolic and carboxylate oxygens of (S)-tyrosine that enable selective N-sulfonylation to be carried out in high yield; (3) the selective phenolic O-alkylation of the tyrosine derivative in high yield with no racemization using aqueous KOH/DMSO; and (4) the selective hydrogenation of the pyridine ring in the presence of the tyrosine ring using Pd/C in acetic acid." @default.
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• W2002249662 date "1993-06-01" @default.
• W2002249662 modified "2023-10-15" @default.
• W2002249662 title "A practical synthesis of fibrinogen receptor antagonist MK-383. selective functionalization of (S)-tyrosine" @default.
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• W2002249662 doi "https://doi.org/10.1016/s0040-4020(01)87943-6" @default.
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