chapter  14
10 Pages

Thiol–Yne Coupling between Propargyl 2,3,4,6-Tetra-O-acetyl-β-d-glucopyranoside and Thiol : Expedient Access to Neoglycolipids

Experimental Methods ........................................................................................... 114 General Methods ............................................................................................... 114

3-(Dodecanylthio)prop-2-enyl 2,3,4,6-Tetra-O-acetyl-β-dglucopyranoside (2) ...................................................................................... 115 2,3-Bis(dodecanylthio)propyl 2,3,4,6-Tetra-O-acetyl-β-dglucopyranoside (3) ...................................................................................... 116 2,3-Bis(dodecanylthio)propyl β-d-Glucopyranoside (4) .............................. 117

Acknowledgments .................................................................................................. 117 References .............................................................................................................. 121

Glycolipids and glycosphingolipids consist of sugar residues that are attached to different lipid backbones.1 Glycolipids are important components expressed at the cell surface where they play numerous roles in biological processes such as immunity and cell signaling, as well as structural roles.2 They form the backbone of both prokaryotic and eukaryotic cell membranes. Novel biological activities involving glycolipids have been continuously discovered in recent years. Consequently, their synthesis as well as those of analogs,3 including glycodendrimersomes,4 has proved useful in understanding these latest functions. In addition, development of neoglycolipid microarrays has witnessed several recent applications toward deciphering their specic biological functions.5