Syntheses of 2-O-glycosyl derivatives of N-acetyl-d-neuraminic acid
1986; Elsevier BV; Volume: 158; Linguagem: Inglês
10.1016/0008-6215(86)84004-6
ISSN1873-426X
AutoresHaruo Ogura, Kimio Furuhata, Masayoshi Itoh, Yoshiyasu Shitori,
Tópico(s)Natural product bioactivities and synthesis
ResumoSyntheses of N-acetyl-d-neuraminic acid derivatives are reported. Methyl 4,7,8,9-tetra-O-acetyl-N-acetyl-2-chloro-2-deoxy-β-d-neuraminate (3) was prepared directly from methyl N-acetyl-β-d-neuraminate (2) in good yield. Koenigs-Knorr reaction of 3 with an excess of methanol gave the methyl α-glycoside of methyl N-acetyl-d-neuraminate (4). 2,3-O-Isopropylidene-d-ribono-1,4-lactone, 2,3-O-isopropylideneuridine, and 5-fluoro-2,3-O-isopropylideneuridine reacted with 3 to give anomeric mixtures of methyl N-acteyl-d-neuraminate derivatives. The stereochemistry of these compounds was confirmed from n.m.r. and c.d. spectra, and measurements of the rate of hydrolysis of the glycosidic bond.
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