Efficient synthesis of new N-alkyl-d-ribono-1,5-lactams from d-ribono-1,4-lactone |
| |
Authors: | Céline Falentin |
| |
Institution: | 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 d-Ribono-1" target="_blank">d-Ribono-1 4-lactone d-ribonamides" target="_blank">N-Alkyl-d-ribonamides d-ribono-1" target="_blank">N-Alkyl-d-ribono-1 5-lactams |
本文献已被 ScienceDirect 等数据库收录! |
|