The synthesis of
4-
O
-alkyl analogues of
N
-acetylneuraminic
acid (Neu5Ac) and the scope of the reaction
are described. Activated alkyl halides and sulfonates and primary
alkyl iodides give products in useful yields. The utility of the methodology
is exemplified using a thiophenyl Neu5Ac building block to synthesize
a 4-
O
-alkyl DANA analogue. These results expand the
toolbox of Neu5Ac chemistry with value in drug discovery and for the
design of novel tools to study the biology of Neu5Ac lectins.