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- W2085307183 abstract "Abstract The reaction of peracetylated N ‐acetylneuraminic acid methyl ester 1 with nitrosyl acetate affords a mixture of anti / syn ‐ N ‐nitroso derivatives 2a and 2a ′, which can be transformed with sodium trifluoroethanolate into the 5‐diazo compound 3 . The reaction of 3 with tetrabutylammonium acetate/acetic acid yields methyl 2,4,5,7,8,9‐hexa‐ O ‐acetyl‐3‐deoxy‐ D ‐ clycero ‐β‐ D ‐ galacto ‐2‐nonulopyranosidonate (KDN) ( 4a ). On the other hand, 5‐azido‐5‐deoxy‐KDN ( 5a ) is formed by treating 3 with hydrazoic acid in toluene. Heating of 2a / 2a ′ in toluene furnishes a mixture of the peracetylated deaminated furanoid sialic acid derivative 10 with probably changed configuration at C‐5 and C‐6 and the deaminated 5,6‐ and 4,5‐didehydrosialic acid derivatives 6 and 7 . Catalytic hydrogenation of 6 and 7 yields the 5‐deoxy‐KDN derivative 9a and ‐ after hydrogen‐olysis of the 4‐acetoxy group ‐ a minor amount of compound 8 . The compounds 4a , 5a , and 9a have been converted into the free deaminated sialic acids 4e , 5e , and 9e via the 4‐me‐thylumbelliferyl 2α‐glycosides 4c , d , 5c , d , and 9c , d ." @default.
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- W2085307183 date "1990-06-12" @default.
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- W2085307183 title "Structural variations onN-acetylneuraminic acid, 16. A convenient approach to 3-deoxy-D-glycero-D-galacto-nonulosonic acid (KDN), 5-azido-5-deoxy-KDN and 5-deoxy-KDN, and their 4-methylumbelliferyl 2α-glycosides" @default.
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- W2085307183 doi "https://doi.org/10.1002/jlac.1990199001107" @default.
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