Acetic Acid → 9-(4-Thio-2,3-dideoxy-D-ribofuranosyl)-2-chloro-6aminopurine

Participants

Reaction Steps

To a solution of 15 (100 mg, 0.19 mmol) in 5 mL of THF was added CH3COOH (14 μL, 0.24 mmol) and 1 M solution of tetrabutylammonium fluoride in MeOH (0.4 mL, 0.4 mmol) followed by stirring for 1 hour. One drop of pyridine was added and then solvent was evaporated in vacuo. The residue was purified by preparative TLC using 90:10 CHCl3 -MeOH as eluant to afford crude 18 which was crystallized by EtOH to give pure 18 (38 mg, 70%); mp. 125°-127° C.; FAB MS 286 (M+H)+ ; 1H NMR (DMSO-d6) δ 8.45 (s, 1, H-2), 7.80 (brs, 2, NH2), 6.10 (m, 1, 1'-H), 5.12 (m, 1, 5'-OH), 3.75 (m, 1, 4'-H), 3.61 (m, 2, 5'-H), 2.40 (m, 2, 2'-H), 2.15 (m, 1, 3'-H), 2.0 (m, 1, 3'-H).

Provenance & Evidence