tert-Butanol → HCID 21672599, compound

To a stirred solution of nucleoside 4 (2.26 g, 4.68 mmol) in THF (12 cm3) and water (12 cm3) was added sodium periodate (3.04 g, 14.2 mmol) and a 2.5% solution of osmium tetraoxide in tert-butanol (w/w, 0.603 cm3, 40 μmol). The solution was stirred at room temperature for 45 min. Water (25 cm3) was added and the solution was extracted with dichloromethane (2×50 cm3). The organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate (3×30 cm3) and dried (Na2SO4). The solvent was removed under reduced pressure and the residue was redissolved in THF (12 cm3) and water (12 cm3). The mixture was stirred at room temperature and sodium boronhydride (182 mg, 4.71 mmol) was added. After stirring for 1.5 h, water (25 cm3) was added and the solution was extracted with dichloromethane (2×50 cm3). The organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate (3×30 cm3) and dried (Na2SO4). The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography using dichloromethane/methanol (98:2, v/v) as eluent to give 5 as a white solid material (1.13 g, 49%). δH (CDCl3) 9.29 (1 H, br s, NH), 7.47 (1 H, d, J 1.1, 6-H), 7.38-7.25 (10 H, m, Bn), 6.22 (1 H, d, J 3.4, 1′-H), 4.62 (2 H, s, Bn), 4.60 (1 H, m, 4′-H), 4.46 (2 H, s, Bn), 4.35 (1H, dd, J 3.4, 7.5, 2′-H), 3.83-3.73 (4 H, m, 2×5′-H, 2×2″-H), 2.67 (1 H, br s, OH), 2.07-2.01 (2 H, m, 2×1″-H), 1.77 (3 H, d, J 0.5, CH3). δC (CDCl3) 164.3 (C-4), 150.3 (C-2), 137.6, 137.4 (Bn, C-6), 136.7 (Bn), 128.6, 128.4, 128.2, 127.8, 127.6, 127.3, 127.1 (Bn), 108.4 (C-5), 88.0, 87.7, 81.6, 74.7 (C-1′, C-2′, C-3′, C-4′), 73.7, 69.6 (Bn), 64.6 (C-5′), 57.7 (C-2″), 28.6 (C-1″), 12.4 (CH3). FAB-MS m/z 483 [M+H]+, 505 [M+Na]+ (Found: C, 63.6; H, 6.2; N, 5.4. C26H30N2O7,0.5H2O requires C, 63.5; H, 6.4; N, 5.7%).

1. extractionthe solution was extracted with dichloromethane (2×50 cm3)
2. washThe organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate (3×30 cm3)
3. dry with materialdried (Na2SO4)
4. customThe solvent was removed under reduced pressure
5. dissolutionthe residue was redissolved in THF (12 cm3)
6. stirringThe mixture was stirred at room temperature
7. additionsodium boronhydride (182 mg, 4.71 mmol) was added
8. stirringAfter stirring for 1.5 h
9. additionwater (25 cm3) was added
10. extractionthe solution was extracted with dichloromethane (2×50 cm3)
11. washThe organic phase was washed with a saturated aqueous solution of sodium hydrogencarbonate (3×30 cm3)
12. dry with materialdried (Na2SO4)
13. customThe solvent was removed under reduced pressure
14. customthe residue was purified by silica gel column chromatography

ORD record

ord-9fc8fa20cf994fc29cb5b11e025f47ef

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08034909B2