Synthetic approach toward complexity of sialic acid-containing glycans

Figures & data

Fig. 1. Structures of sialic acids and ganglioside GM3.

Note: Arrows point possible sites to be modified with various substituents indicated above or below each arrow in inter- or intramolecular manner.

Fig. 2. Efficient conversion to sialic acid congeners for N-Troc-sialoside.

Fig. 3. Synthesis of GAA-7 glycan.

Notes: CAc, chloroacetyl; MS, molecular sieves; NIS, N-iodosuccinimide; TTBP, 2,4,6-tri-tert butylpyrimidine.

Fig. 4. Elevated reactivity of C-4 and C-8 hydroxyl groups in 1,5-lactamized sialic acid derivatives.

Fig. 5. (a) Synthesis of Hp-s6 glycan. (b) Structures of HPG-1 and HPG-7 glycans.