Acetic Acid → HCID 10515470, compound

Methyl 5-deoxy-2,3-di-O-acetyl-L-ribofuranoside (33 g, 15.2 mmol) was dissolved in acetic acid (20 mL) and acetic anhydride (5 mL). The solution was cooled to ice bath temperatures and concentrated sulfuric acid was added dropwise (1 mL). The solution was kept at 5° C. for 4 days, then it was poured into ice water (50 mL) and extracted with 3:1 ethyl acetate hexanes (200 mL and 75 mL). The combined organics were washed with 10% sodium biarbonate (2×50 mL) and water (50 mL). The organic layers were dried, and concentrated and the residue purified on a silica gel column (5×15 cm, 230-400 mesh) with ethyl acetate:hexanes (1:3). Both anomers were observed but were isolated together as a clear oil (2.2 g, 8.8 mmol, 58%); 1H NMR (DMSO-d6) δ5.96 (d, 1H J=1 Hz), 5.23 (d, 1H, H-2, J=5 Hz), 4.96 (t, 1H, H-3, J=5.7 Hz), 4.24-4.16 (m, 1H, H-4), 2.07 (s, 3H, OAc), 2.05 (s, 3H, OAc), 2.02 (s, 3H, OAc), 1.27 (d, 3H, H-5, J=6.3 Hz).

1. additionwas added dropwise (1 mL)
2. extractionextracted with 3:1 ethyl acetate hexanes (200 mL and 75 mL)
3. washThe combined organics were washed with 10% sodium biarbonate (2×50 mL) and water (50 mL)
4. customThe organic layers were dried
5. concentrationconcentrated
6. customthe residue purified on a silica gel column (5×15 cm, 230-400 mesh) with ethyl acetate:hexanes (1:3)

ORD record

ord-364fc100af944663ba976f945145d002

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06204249B1