Abstract: Described are glycolipids having a saccharide moiety attached at the 2-position of the lipid chain (i.e., “2-hydroxy glycolipids”), glycolipids having a saccharide moiety attached at the 4-position of the lipid chain (i.e., “4-hydroxy glycolipids”), and derivatives thereof. Further described are synthetic methods for preparing 2-hydroxy glycolipids, 4-hydroxy glycolipids, and derivatives thereof.

Abstract: Methods of forming a glycolipid are disclosed. A method may include glycosylating a sugar with a beta-hydroxyester using BF3-L as a glycosylation promoter. L may include one or more of Diethylether, Tetrahydrofurn, Dimethyle Sulfide, or combinations thereof. The beta-hydroxyester may include a carbon length ranging from C2 to C24. The sugar may be a protected sugar that includes peracetylated-rhamnose, peracetylated-xylose, peracetylated-glucose, peracetylated-galactose or combinations thereof. The beta-hydroxyester and sugar may be combined in a reaction vessel to form a mixture. A solvent may be added to the mixture to substantially dissolve the mixture. The glycosylation promoter may be added to the solution such that the solution is maintained withing a desired temperature range.

Abstract: Methods of carbohydrate acetylation are disclosed. A method may include adding a carbohydrate to a reaction vessel, adding poly-4-vinylpyriding (P4VP) to the reaction vessel, adding a bio-derived solvent to the reaction vessel, adding acetic anhydride (Ac20) to the reaction vessel, and adding a catalyst to the reaction vessel. The bio-derived solvent may be 2-methyltetrahydrofuran (2-MeTHF). A catalyst may also be added to the reaction vessel.