As part of glycoconjugate family, glycolipids and glycopeptides are involved in a variety of important biological, physiological and pathological processes, such as cell-cell interactions, viral and bacterial infections, immune response, cancer progression, etc. Synthesis of glycoconjugate mimics has attracted intensive research interest for biological and pharmaceutical applications. This thesis was devoted to the synthesis of N-oxyamide-linked glycolipids and glycopeptides, since N-oxyamide-containing compounds have shown improved metabolic stability, and interesting secondary structures due to the easy H-bond formation property of N-oxyamide compounds.From methyl alpha-D-glucopyranoside, the 2,6-functionalized pyranoid glycoaminooxy acid derivatives have been successfully prepared as a multifunctional building block for further derivatization to new N-oxyamide glycolipids. From glucose or galactose pentaacetate and (S)-1,2-di-O-benzyl-glycerol, we have successfully achieved the first synthesis of N-oxyamide-linked beta-glycolipids with one or two lipids chains, as novel mimics of glycoglycerolipids and glycosphingolipids.In addition, the (2R) and (2S)-3-beta-O-glycosyl aminooxy esters have been stereoselectively synthesized from (2R)-beta-glycoglycerol, with Mitsunobu reaction and Lattrell-Dax epimerization as key steps. N-Oxyamide-linked glycopeptides have been prepared from the orthogonally protected glycosyl aminooxy esters.