Prespacer Glycosides in Glycoconjugate Chemistry. Dibromoisobutyl (DIB) Glycosides for the Synthesis of Neoglycolipids, Neoglycoproteins, Neoglycoparticles, and Soluble Glycosides
3-Bromo-2-(bromomethyl)propyl (dibromoisobutyl or DIB) mono- to tetrasaccharide glycosides were prepared in moderate to high yields by treatment of the corresponding 1-0-acetyl saccharides with 3-bromo-2-(bromo-methyl)propanol (DIBOL) and boron trifluoride etherate. Treatment of the DIB glycosides with alkyl- and ω-methoxycarbonylalkyl thiols gave the corresponding bis-sulfide glycolipids and spac