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Structural variations ofN-acetylneuraminic acid, 23. Synthesis of 2-deoxy-2Heq-sialic Acid analogues structurally varied at C-4

✍ Scribed by Hartmann, Michael ;Zbiral, Erich

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
772 KB
Volume
1991
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

2‐Deoxy‐2‐H~eq~‐N‐acetylneuraminic acid (1a) has been shown to be a versatile mimic for sialosyl 2‐α‐glycosides to study the hemagglutinin‐sialic acid interaction. Starting with a 4‐oxo derivative of 2‐deoxy‐2‐H~eq~‐sialic acid, we obtained the 4‐C‐methyl~ax~ and 4‐C‐methyl~eq~ derivatives 4 and 5 as a separable mixture. The derivative 4 was formed as a single product by using tributoxymethylzirconium. The 4‐C‐methylene derivative 10 was formed by treatment of the ketone with Cp~2~ZrCl~2~/Zn/CH~2~I~2~. Catalytic hydrogenation of the exo‐methylene compound 10 yielded the two 4‐deoxy‐4‐C‐methyl diastereomers 13 and 14. All above‐mentioned derivatives could be transformed into the unprotected 4‐branched 2‐deoxy‐2‐H~eq~‐sialic acids 7, 9, 12, 16, and 18. 2‐Deoxy‐2H~eq~‐4‐oxosialic acid (21) was synthesized by a different pathway.

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