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TCI Practical Example: Protection of a Diol Moiety Using TIPDSCl2
We are proud to present the selective cyclic silyl protection of hydroxy groups at 3'- and 5'-positions of uridine by using TIPDSCl2.
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Used Chemicals
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Procedure
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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.
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Experimenter's Comments
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The reaction solution was monitored by UPLC.
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Analytical Data
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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).
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Lead Reference
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- Preparation of Zwitterionic Ribonucleoside Phosphoramidites for Solid-Phase siRNA Synthesis
