Ru-catalyzed metathesis of octadienylether xyloside

The reaction of the octadienylether of xylosyle and of its peracetylated form in the presence of Grubbs catalysts has led to O-allyl carbohydrates, and from the protected carbohydrate, to the bolaform with a C4 tether. The concomitant formation of cyclopentene, highlighted from analysis of the crude reaction by mass spectroscopy, led to propose a mechanistic scheme involving both double bonds of the substrate.