Trichloroacetonitrile → 2,3,4-Tri-o-acetyl-alpha-l-fucopyranosyl trichloroacetimidate

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Reaction Steps

Sodium hydride (0.25 g, 10.9 mmol) is added under nitrogen and at room temperature to a mixture of 2,3,4-tri-O-acetyl-L-fucopyranose (anomer mixture) (2.00 g, 6.89 mmol) and trichloroacetonitrile (7.0 ml, 70 mmol) in 20 ml of dry dichloromethane. The mixture is stirred for about 12 h and then filtered through kieselguhr and concentrated. After chromatographic purification (petroleum ether/ethyl acetate 3:1), O-(2,3,4-tri-O-acetyl-α-L-fucopyranosyl) trichloroacetimidate (3) is obtained in a yield of 71% (2.13 g).

Provenance & Evidence