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• W2079423107 abstract "N-Acetylneuraminic acid (Neu5Ac) and [6-2H]-Neu5Ac were prepared from 2-acetamido-2-deoxy-d-glucose (N-acetyl-d-glucosamine). The Henry reaction of a 1-deoxy-1-nitro derivative of GlcNAc (protected 1-C-nitroanhydro-d-glucitol) with cyclohexylidene-d-glyceraldehyde, followed by successive acetylation and reductive denitration with Bu3SnH, gave an anhydrononitol intermediate (6) diastereoselectively in high yields. Debenzylidenation of 6 freed its distal primary carbinol group, which was subjected to catalytic oxidation followed by hydrolysis, esterification (diazomethane), and acetylation to give a protected methyl nononate. This ester was transformed into the known methyl N-acetyl-4,7,8,9-tetra-O-acetyl1-2,3-dehydroneuraminate (15), which was identical with a sample prepared from Neu5Ac. Neu5Ac was obtained from 15 by bromoetherification (NBS, methanol) followed by reductive debromination with Bu3SnH and hydrolysis. Similarly, the [6-2H]-derivative of 15 was transformed into [6-2H]-Neu5Ac." @default.
• W2079423107 created "2016-06-24" @default.
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• W2079423107 date "1987-07-01" @default.
• W2079423107 modified "2023-10-14" @default.
• W2079423107 title "A synthesis of N-acetylneuraminic acid and [6-2H]-N-acetyl-neuraminic acid from N-acetyl-d-glucosamine" @default.
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• W2079423107 doi "https://doi.org/10.1016/0008-6215(87)80145-3" @default.
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