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ChemicalBook CAS DataBase List N-Isobutyryl-5'-O-tert-butyldiMethylsilyl-2'-deoxyguanosine, 97%
85326-10-9

N-Isobutyryl-5'-O-tert-butyldiMethylsilyl-2'-deoxyguanosine, 97% synthesis

2synthesis methods
-

Yield:85326-10-9 74%

Reaction Conditions:

with sodium chloride in chloroform;N,N-dimethyl-formamide;

Steps:

R.2 Production of N2-isobutyryl-5'-O-(tert-butyldimethylsilyl) -2'-deoxyguanosine

Reference Example 2 Production of N2-isobutyryl-5'-O-(tert-butyldimethylsilyl) -2'-deoxyguanosine N2-isobutyryl-2'-deoxyguanosine (20.5 g) was dissolved in 200 ml of DMF. After 18.5 g of imidazole was dissolved in the resultant solution by addition, 21.4 g of tert-butyldimethylsilyl chloride was then added. DMF (100 ml) was further added and the solution was stirred at room temperature. After 8 hours, extraction using chloroform was carried out and the organic layer was washed by a saturated aqueous solution of sodium chloride and dried with anhydrous magnesium sulfate. After concentration of the extract, the target compound was separated by column chromatography (methanol/chloroform). The fraction solution including the target compound was prepared and concentrated to obtain 20.5 g of the titled compound (yield; 74%). 1H NMR (400 MHz, CDCl3) δ: 12.4(1H, s), 10.9(1H, s), 8.0(1H, s), 6.0(1H, dd, J=6.4, 6.4 Hz), 4.6(2H, m), 4.1(1H, d, J=2.0 Hz), 3.8(2H, m), 2.9(1H, m), 2.4(2H, m), 1.3(6H, m), 0.8(9H, s), 0.02(6H, s)

References:

US2003/9028,2003,A1