Triethylamine → Oleyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranoside

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A solution of 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranose (2.0 g, 6.5 mmol) and oleyl iodide (2.5 g, 6.6 mmol) in dichloromethane (40 ml) containing triethylamine (1 ml) is kept under nitrogen for 2 days at room temperature. The solution is worked up in the normal manner and the resulting syrup is column chromatographed on silica gel with 2-10% ethyl acetate in chloroform as eluents. Oleyl 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranoside is isolated as a syrup (1.2 g, 32%), [α]D +26° (c, 2.19, chloroform).

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