Synthesis of sialic acid-containing nucleotide sugars: CMP-sialic acid analogs

✍ Scribed by Kiyoshi Ikeda; Yoshihiro Nagao; Kazuo Achiwa

• Publisher: Elsevier Science
• Year: 1992
• Tongue: English
• Weight: 658 KB
• Volume: 224
• Category: Article
• ISSN: 0008-6215
• DOI: 10.1016/0008-6215(92)84099-e

✦ Synopsis

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).