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Glycoproteins are characterized by their complexity and diversity. To clarify their functions, synthetic approaches are considered to be promising. Synthesis of biomacromolecules is an important subject in organic synthesis. Establishment of sophisticated technologies in peptide and nucleic acid synthesis has played key roles in molecular, cellular, and structural biology. Chemical synthesis of oligosaccharides has been more elusive. Development of synthetic methodologies useful for efficient and facile preparation of glycoprotein glycan is a focal issue in carbohydrate chemistry. In light of their structural diversity, practical strategy to speed-up the synthesis of oligosaccharide is expected to be highly valuable. A major portion of our research has activities has been focused on stereoselective synthesis of glycoconjugate oligosaccharides, which resulted in developments of novel methodologies toward -sialoside and several types of 1,2-cis glycosides.1-3 Using these methodologies, syntheses of several types of novel glycoprotein glycans were conducted. Recently, a systematic strategy to synthesize glycoprotein glycans that play important roles in glycoprotein quality control, was established. With structurally defined glycans and in hand, analyses of various enzymes, lectins, and chaperones, which are involved in glycoprotein processing in the ER, were conducted, revealing their specificities in a quantitative manner. 4-8