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Synthesis of new N-substituted 3,4,5-trihydroxypiperidin-2-ones from d-ribono-1,4-lactone by Céline Falentin-Daudre; Daniel Beaupère; Imane Stasik-Boutbaiba is a Biochemistry, Genetics and Molecular Biology article available to read on EtoBox.

What is Synthesis of new N-substituted 3,4,5-trihydroxypiperidin-2-ones from d-ribono-1,4-lactone about?

D-Ribono-1,4-lactone was treated with ethylamine in DMF to afford N-ethyl-D-ribonamide 8a in quantitative yield. Using this reaction procedure, N-butyl, N-hexyl, N-dodecyl, N-benzyl, N-(3-methylpyridinyl)-, N-(2-hydroxy-ethyl)-, and N-(2-cyano-ethyl)-D-ribonamides 8b-h were obtained in quantitative yield. Bromination of the amides 8a-e with acetyl bromide in dioxane followed by acetylation gave 2,3,4-tri-O-acetyl-5-bromo-5-deoxy-N-ethyl, N-butyl, N-hexyl, N-dodecyl, and N-benzyl-D-ribonamides 9a-e in 40-54% yields. To obtain 2,3,4-tri-O-acetyl-5-bromo-5-deoxy-N-(3-methyl-pyridinyl)-, N-(2hydroxy-ethyl)-, and N-(2-cyano-ethyl)-9f-h, the bromination is necessary before the amidation reaction. Treatment of the bromoamides 9a-h with NaH in DMF followed by methanolysis affords N-alkyl-D-ribono-1,5-lactams 12a-h in quantitative yield.

Who reads Synthesis of new N-substituted 3,4,5-trihydroxypiperidin-2-ones from d-ribono-1,4-lactone?

Author

Céline Falentin-Daudre; Daniel Beaupère; Imane Stasik-Boutbaiba

Publisher

Elsevier Science; Elsevier ; Elsevier Ltd.; Elsevier BV (ISSN 0008-6215)

Published

2010

Language

EN

Field

Biochemistry, Genetics and Molecular Biology (Life Sciences)