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Synthesis of sialic acid-containing nucleotide sugars: CMP-sialic acid analogs.
Syntheses of some sialic acid-containing nucleotide sugars are reported. The reaction of methyl [(2-hydroxy)ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galacto -2-nonulopyranosid]onate (4) with various fully protected hydrogen phosphonates of nucleosides (5a-c) in the presence of 2,4,6-triisopropylbenzenesulfonyl chloride (TPSCl), gave, after oxidation and deprotection, the corresponding sialic acid-containing nucleotide sugar analogs (8a-c).
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