Glycolipids play numerous important roles in various disease states and immune response. For example, KRN7000, a slightly simplified analog of the series of naturally occurring glycosphingolipids of marine origin (Agelasphins), is a powerful immnunostimulant. It activates natural killer T cells (NKT cells) by first binding to antigen presenting CD1d molecules. Structural studies have shown that the lipid part of KRN-7000 binds to the hydrophobic pockets of the CD1d cell and the exposed sugar part is presented to the invariant T-cell antigen receptor (TCR). This CD1d-restricted activation of NKT cells is enhanced by the corresponding C-glycoside analog. Recently, there has been interest in studying immunoresponsive glycolipids of bacterial origin from Sphingomonas paucimobilis (e.g. GSL1') and Borrelia burgdorferi (e.g. BBGL2) species. There is growing evidence that these galactolipids show similar a structure-activity profile as that of KRN7000 for CD1d restricted activation of NKT cells. Their C-glycoside analogs are also attractive targets. Stereoselective formation of O and C-glycosidic bond is one of the central challenges in carbohydrate synthesis. In this pursuit, we have employed glycosyl iodides as unique glycosyl donors to construct functionally enriched carbon-appendages on the anomeric center of the sugar moiety in a highly efficient and stereoselective manner. These constructs are used to rapidly synthesize various O-and C-glycoside analogs for biological evaluations. Short and efficient synthesis of KRN7000, GSL1' and their congeners as well as C-glycoside analogs of BBGL2 is presented.