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Structural variations of N ‐acetylneuraminic acid, 23. Synthesis of 2‐deoxy‐2H eq ‐sialic Acid analogues structurally varied at C‐4
Author(s) -
Hartmann Michael,
Zbiral Erich
Publication year - 1991
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1991199101136
Subject(s) - chemistry , sialic acid , diastereomer , methylene , derivative (finance) , stereochemistry , n acetylneuraminic acid , glycoside , medicinal chemistry , biochemistry , financial economics , economics
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.