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Efficient synthesis of new N-alkyl-d-ribono-1,5-lactams from d-ribono-1,4-lactone
Authors:  line Falentin
Affiliation:Laboratoire des Glucides, UMR 6219, Université de Picardie Jules Verne, 33 Rue Saint-Leu, F-80039 Amiens, France
Abstract: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 SOBr2 in DMF or PPh3/CBr4 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%).
Keywords:Azasugars     smallcaps"  >d-Ribono-1,4-lactone   N-Alkyl-  smallcaps"  >d-ribonamides   N-Alkyl-  smallcaps"  >d-ribono-1,5-lactams
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