Topics Archives
[Practical Example]▶ Protection of a Diol Moiety Using TIPDSCl2
TCI Practical Example에서는 TCI의 합성 담당 연구원이 직접 겪은 반응 사례를 분석 자료와 함께 소개하고 있습니다.
[20240401]
"Selective cyclic silyl protection of hydroxy groups at 3'- and 5'-positions of uridine by using TIPDSCl2"
Used Chemicals
Procedure
Uridine (1.0 g, 4.10 mmol) was added to pyridine (13.7 mL) at room temperature and stirred, then TIPDSCl2 (1.42 g, 4.50 mmol) was added. The reaction mixture was stirred for 7 hours. After ethyl acetate (10 mL) was added to the reaction solution, the organic layer was washed with 0.05 mol/L HCl (10 mL), ion exchanged water (10 mL), and brine (10 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (dichloromethane:methanol = 10:1) to afford 1 (1.38 g, 69% yield) as a white solid.
Experimenter's Comments
The reaction solution was monitored by UPLC.
Analytical Data
Compound 1
1H NMR (400 MHz, CDCl3); δ 8.45 (s, 1H), 7.66 (d, J = 8.1 Hz, 1H), 5.73 (s, 1H), 5.68 (d, J = 7.9 Hz, 1H), 4.39 (m, 1H), 4.21 (m, 2H), 4.09 (m, 1H), 4.02 (m, 1H), 2.98 (s, 1H), 1.10 (m, 28H).
Lead Reference
- Preparation of Zwitterionic Ribonucleoside Phosphoramidites for Solid-Phase siRNA Synthesis
첨부파일 | 선택된 파일 없음 |
---|