反应 #1435756

反应方程式

SnCl4

5-iodouracil

2-O-(acetoxymethyl)-1,3-di-O-benzylglycerol

NaHCO3

→

title compound 45

收率 95.0%

1-[[1,3-Bis(benzyloxy)-2-propoxy]methyl]-5-iodouracil

收率 95.0%

溶剂

CH2Cl2

CHCl3

反应条件

后处理

1. 1
   其他prepared
2. 2
   温度The resulting clear solution was cooled to 0° C.
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature overnight
4. 4
   萃取The aqueous layer was extracted with CHCl3
5. 5
   其他the combined organic phase was evaporated
6. 6
   其他The residue was purified by flash chromatography on silica gel eluting with CH2Cl2/MeOH (97:3)

实验过程

To a suspension of 2-O-(acetoxymethyl)-1,3-di-O-benzylglycerol (44; prepared according to Martin J. C., Dvorak C. A., Smee D. F., Matthews T. R., Verheyden J. P. H. (1983) 9-[(1,3-Dihydroxy-2-propoxy)methyl]quanine: a new potent and selective antiherpes agent, J. Med. Chem. 26, 759–761) (2.038 g, 5.9 mmol) and 5-iodouracil (2.106 g, 8.85 mmol) in anhydrous CH2Cl2 (25 mL) at room temperature was added N,O-bis-(trimethylsilyl)acetamide (BSA, 5.46 mL, 22.13 mmol), and the mixture was stirred at room temperature under nitrogen for 2 h. The resulting clear solution was cooled to 0° C., and SnCl4 (1 M solution in CH2Cl2, 5.9 mL, 5.9 mmol) was added. The mixture was stirred at room temperature overnight, and then poured into a mixture of saturated aqueous NaHCO3 and CHCl3. The aqueous layer was extracted with CHCl3, and the combined organic phase was evaporated. The residue was purified by flash chromatography on silica gel eluting with CH2Cl2/MeOH (97:3) to give the title compound 45 as a yellow oil (2.935 g, 95%). 1H NMR (CDCl3) δ 8.59 (s, 1H, NH), 7.82 (s, 1H, H-6), 7.36–7.26 (m, 10H, arom.), 5.28 (s, 2H, CH2N), 4.50 (s, 4H, 2 CH2), 3.99 (m, 1H, CHO), 3.52 (m, 4H, 2 CH2O).

来源