Water → HCID 67728932, compound

Participants

Reaction Steps

To 0.69 g (2.33 mmol) of 9-(2-amino-2-deoxy-β-D-glucopyranosyl)adenine was added 3.45 mL of H2O. To this solution was added a 28 mL 1,4-dioxane solution of 0.94 g (2.80 mmol) of N-(9-fluorenylmethoxycarbonyloxy)succinimide. This resulted in a cloudy mixture. To this system was added 0.13 g (1.50 mmol) of NaHCO3. This mixture was stirred for 12 h at room temperature. At this time, TLC indicated the consumption of starting material and the mixture was concentrated in vacuo to a dry residue. This residue was stirred for 18 h in 250 mL of Et2O and 250 ml of H2O. The suspension was then filtered and the solid dried in a vacuum oven for 2 days. Thus was obtained 1.0 g (82%) of the desired 9-[2-deoxy-2-[[(9H-fluoren-9-ylmethoxy)carbonyl]-amino]-β-D-glucopyranosyl]adenine 1H NMR: (DMSO-d6): adenine aromatic 8.19 (s, 1H), adenine aromatic 8.17 (s, 1H), anomeric H-1 6.60 (d, 1H), Fmoc-methine 4.17 (m, 1H). FAB-MS: m/z 519 for (M+1)+.

Provenance & Evidence