反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
PROCEDURE
实验过程
Compound 30 (1.22 g, 7.25 mmol) was glycosylated as described for the preparation of 6, requiring HMDS (35 mL), benzoyl-blocked sugar (5: 4.4 g, 8.7 mmol) and TMS-triflate (2.0 mL, 10.3 mmol). After stirring overnight at room temperature, the reaction mixture was refluxed for 2 days and then worked up in the usual manner. The crude mixture was subjected to flash silica gel column chromatography using a gradient of methylene chloride to methylene chloride-acetone 10:1 (v/v) and yielded two products. The first to elute from the column was assumed by 1H NMR to be a bis-glycoside which amounted to 660 mg. The second and major product off the column was obtained as a foam and assigned as the desired 3-ribosyl isomer by UV and 1H NMR: yield 1.04 g (24%): UV λmax (EtOH) 232 nm (ε), 283 (): 1H NMR (DMSO-d6) δ 6.34 (t, 1H, C1 ,H), 7.39-7.98 (m, 17H, benzoyl aromatics and NH2, 8.19 (s, 1H, C5H), and other sugar protons. Anal. Calcd. for C, 60.78: H, 3.95: N, 9.15: S, 5.23. Found: 3.93: N, 8.13: S, 4.85.
WORKUP
后处理
- customas described for the preparation of 6
- temperaturethe reaction mixture was refluxed for 2 days
- customyielded two products
- washThe first to elute from the column
- customThe second and major product off the column was obtained as a foam