The in situ generation and subsequent cycloaddition of glycosyl nitrile oxides to norbornadiene (NBD) afforded monomeric isoxazolino norbornenes bearing xylose, glucose, and mannose residues in high yields. Ring-opening metathesis polymerization (ROMP) of the norbornene derivatives containing acetyl-protected sugar residues initiated by Ru(CHPh)(Cl)(2)(PCy3)(2) (1) and Mo(CHCMe2Ph)(N-2,6-(Pr2C6H3)-Pr-i)(O'Bu)(2) (3) proceeded in a living manner with quantitative initiation, affording polymers with narrow molecular weight distributions (M,1 M-n = 1.11-1.35). The living nature of this polymerization by 1 was further demonstrated by the preparation of diblock copolymers in a precise manner by the sequential polymerization of norbornene and its carbohydrate derivatives. Polymers bearing multiple sugar units bearing free sugars were prepared by the deacetylation of the glycopolymers; under basic conditions, and olefinic double bonds in these ROMP polymers were hydrogenated exclusively by p-toluenesulfonhydrazide in chlorobenzene without cleavage of the sugar functionality.