Mirjana Popsavin, V. Popsavin, N. Vukojević
1994
Citations
0
Influential Citations
15
Citations
Journal
Collection of Czechoslovak Chemical Communications
Abstract
A novel synthesis of 1- O -acetyl-2,3,5-tri- O -benzoyl-D-ribofuranose ( I ) has been described starting from 1,2:3,5-di- O -cyclohexylidene-α-D-xylofuranose ( II ), obtained directly from the crude xylose syrup originated from corncobs. Partial acid hydrolysis of II gave 1,2- O -cyclohexylidene-α-D-xylofuranose (III). Selective benzoylation of primary C-5 hydroxyl group of III followed by tosylation of C-3 hydroxyl group afforded IV in an overall yield of 67%. Mild acid methanolysis of IV gave the corresponding methyl xylofuranosides V which were further benzoylated to afford 2,5-di- O -benzoyl derivatives VI in 65% yield. Solvolysis of VI in 95% DMF gave a mixture of 2,5- and 3,5-di- O -benzoylribofuranosides VII , which were subsequently converted into the corresponding tribenzoates VIII . An acetolysis of VIII afforded I in an overall yield of 96% related to VI .