Di-tert-butylsilyl Bis(trifluoromethanesulfonate)

Used Chemicals

• Uridine [U0020]
• 2,6-Lutidine [L0067]
• Di-tert-butylsilyl Ditriflate [D3135]
• DMF

Procedure

Di-tert-butylsilyl ditriflate (0.6 mL, 2.0 mmol) was added dropwise to the solution of uridine (400 mg, 2.0 mmol) and 2,6-lutidine (0.38 mL, 3.3 mmol) in DMF (7 mL) for over 5 minutes at 0 °C. The reaction mixture was stirred for 2 hours at room temperature. Ion exchanged water (20 mL) was added to the reaction mixture, and the aqueous layer was extracted with a mixture of hexane (30 mL) and ethyl acetate (6 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel chromatography (dichloromethane:methanol = 95:5) to give 1 (501 mg, 79.5% 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 8.76 (s, 1H), 7.17 (d, J = 8.1 Hz, 1H), 5.69 (d, J = 8.0 Hz,1H), 5.55 (s, 1H), 4.40 (m, 1H), 4.34 (m, 1H), 4.10 (m, 1H), 3.93 (m, 2H), 1.01 (s, 9H), 0.96 (s, 9H).

Other References

• A Claisen Approach to 4′-Ed4T
• W. P. Gallagher, P. P. Deshpande, J. Li, K. Katipally, J. Sausker, Org. Lett. 2015, 17, 14.

References

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• V. Serebryany, L. Beigelman, Tetrahedron Lett. 2002, 43, 1983.
• K. Furusawa, Busshitsu Kagaku Kogyo Kenkyusho Hokoku 1994, 2, 337.
• Efficient synthesis of N2-dimethylaminomethylene-2’-O-methylguanosine
  • T. Mukobata, Y. Ochi, Y. Ito, S. Wada, H. Urata, Bioorg. Med. Chem. Lett. 2010, 20, 129.