Trityl Chloride

• 1,2-O-Isopropylidene-α-D-xylofuranose [I0721]
• Trityl Chloride [C0308]
• Triethylamine [T0424]
• Dichloromethane

To a solution of 1,2-O-isopropylidene-α-D-xylofuranose (200 mg, 1.1 mmol) in dichloromethane (2 mL) was added triethylamine (0.22 mL, 1.6 mmol) and stirred at room temperature for 1 hour. A solution of trityl chloride (323 mg, 1.2 mmol) in dichloromethane (1 mL) was added to the reaction mixture and stirred at room temperature for 3 hours. The reaction mixture was quenched with water and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane = 1:4, Rf = 0.15) to give 1 as a white solid (432 mg, 95% yield).

The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:4, Rf = 0.15).

1,2-O-Isopropylidene-5-O-trityl-α-D-xylofuranose (1)

¹H NMR (270 MHz, CDCl₃); δ 7.46-7.22 (m, 15H), 6.01 (d, J = 3.8 Hz, 1H), 4.53 (d, J = 3.8 Hz, 1H), 4.27-4.25 (m, 2H), 3.57 (dd, J = 10.3, 5.1 Hz, 1H), 3.49 (dd, J = 10.3, 5.1 Hz, 1H), 3.16 (d, J = 2.7 Hz, 1H), 1.49 (s, 3H), 1.33 (s, 3H).

• Karrikins from plant smoke modulate bacterial quorum sensing
• A. Mandabi, H. Ganin, J. Rayo, M. M. Meijler, Chem. Commun. 2014, 50, 5322.