Synthesis of an oligosaccharide

Deoxy-sugars. Part XVIII. Synthesis of an Oligosaccharide by the Thermal Condensation of ap-Methyl-2-deoxy-D-ga actofuranoside, W. G. Overend, F. Shafizadeh, and M. Stacey, /. Chem. Soc., (1951)994-997. 

Yamago S, Yamada T, Ito H, Hara O, Mino Y, Yoshida J. Combinatorial synthesis of an oligosaccharide library by using beta-bromoglycoside-mediated iterative glycosylation of seleno-glycosides rapid expansion of molecular diversity with simple building blocks. Chem. Eur. J. 2005 11 6159-6174. 

In another report of polymer-supported synthesis of an oligosaccharide Cp2HfCl2-AgOTf was used for activation of glycosyl fluoride on a resin (Fig. 6) [12a]. 

Scheme 17.4 An early example of the synthesis of an oligosaccharide using nitroveratryl linker (4).

The dibromide 48 so obtained can undergo coupling reactions with NPGs to give the corresponding disaccharides. An example of this strategy is shown in Scheme 31 for the synthesis of an oligosaccharide of the manno series. 

Strategies for Synthesis of an Oligosaccharide Library Using a Chemoenzymatic Approach... 

The synthesis of an oligosaccharide with 1,4-glycosidic linkage using a polymer support has yet to be reported. 

This is another example of synthesis of an oligosaccharide through stepwise addition of monosaccharide blocks. But in sharp contrast to the previously described achievement, it is representative of a nonconventional construction of a linear oligosaccharide starting from the nonreducing end of the oligomer. The protected tetrasaccharide is built up from two precursors as shown in Scheme 7. 

This is the first synthesis of an oligosaccharidic fragment of heparin with a prominent biological activity [23]. 

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