5'-Trt-N6-Bz-2'-dA synthesis
- Product Name:5'-Trt-N6-Bz-2'-dA
- CAS Number:75759-62-5
- Molecular formula:C36H31N5O4
- Molecular Weight:597.66
Yield:75759-62-5 81%
Reaction Conditions:
with pyridine at 20; for 24 h;
Steps:
N6-Benzoyl-5 ' -O-trityl-2 ' -deoxyadenosine (2c).
N6-Benzoyl-2 ' - deoxyadenosine (lc, 1.07 g, 3.0 mmol, 1 eq. ) was dissolved in anhydrous pyridine (30 mL) , and trityl chloride (1.00 g, 3.6 mmol, 1.2 eq.) was added. After stirring at room temperature for 1 day, the reaction mixture was poured into saturated sodium bicarbonate solution (200 mL) and the precipitate was collected by suction filtration, washed with water and hexane . The obtained crude product was purified by silica gel column chromatography (dichloromethane/methanol : 30:1) to give N6-Benzoyl-5 ' -O-trityl- 2 ' -deoxygadenosine 2c (1.45 g, 81%) as a white solid. XH NMR (400 MHz, CDC13) δ 9.12 (s, 1H) , 8.74 (s, 1H) , 8.15 (s, 1H) , 8.08 - 8.00 (m, 2H) , 7.62 (m, 1H), 7.52 (m, 2H), 7.46 - 7.38 (m, 6H), 7.34 - 7.20 (m, 9H) , 6.50 (t, J = 6.5 Hz, 1H), 4.74 (d, J = 4.7 Hz, 1H), 4.19 (td, J = 4.8, 3.5 Hz, 1H) , 3.49 - 3.42 (m, 2H) , 2.90 (m, 1H) , 2.58 (m, 1H) .
References:
WO2017/87887,2017,A1 Location in patent:Page/Page column 81; 82