Protecting Group Strategies in Carbohydrate Synthesis

Shang-Cheng Hung1 and Cheng-Chung Wang2 

1Genomics Research Center, Academia Sinica, Taipei, Taiwan 2Institute of Chemistry, Academia Sinica, Taipei, Taiwan 

Glycochemical Synthesis Strategies and Applications, First Edition. 

Edited by Shang-Cheng Hung and Medel Manuel L. Zulueta. 

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A review on protective group strategies in carbohydrate synthesis has appeared which included consideration of the preparation of phosphate and sulphate esters of heparin oligosaccharides, and a related article covered the detailed consideration of the binding domains associated with the heparin-antithrombin 3 complex. ... 

The total synthesis of GM2 presented here is an introductory exercise in carbohydrate chemistry. During the synthesis the importance of a suitable protecting group strategy to achieve the desired stereochemistry has been pointed out. There are reactions specific for carbohydrates and many other transformations, which can be utilized in non-carbohydrate-synthesis , too. However there is no ideal way in carbohydrate chemistry. Each synthesis has been optimized for the respective sugar. 

In this chapter we will summarize chemical methods for the stereoselective attachment of carbohydrates to amino acids, with particular emphasis on the preparation of building blocks for use in solid-phase glycopeptide synthesis based on the 9-fluorenylmethoxycarbonyl (Fmoc) protective group strategy. 

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