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Efficient synthesis of new N-alkyl-d-ribono-1,5-lactams from d-ribono-1,4-lactone

✍ Scribed by Céline Falentin; Daniel Beaupère; Gilles Demailly; Imane Stasik

Publisher
Elsevier Science
Year
2009
Tongue
French
Weight
683 KB
Volume
50
Category
Article
ISSN
0040-4039

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✦ Synopsis

D-Ribono-1,4-lactone was treated with ethylamine in DMF to afford N-ethyl-D-ribonamide 9a in quantitative yield. Bromination of amide 9a by the system SOBr 2 in DMF or PPh 3 /CBr 4 in pyridine led, after acetylation, to epoxide 7. However, treatment of amide 9a with acetyl bromide in dioxane followed by acetylation gave 2,3,4-tri-O-acetyl-5-bromo-5-deoxyl-N-ethyl-D-ribonamide 10a. Methanolysis of 10a, with sodium methoxide, afforded the N-ethyl-D-ribonolactam 11a in 51% overall yields. Using this method, N-butyl, N-hexyl, N-dodecyl, and N-benzyl-D-ribonolactams 11b-e were obtained in good yields (48-53%).

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