Preparation of ether-linked 2-acetamido-2-deoxy β-glycolipids via zinc chloride promoted coupling of Ac4GlcNAc-CI with lipid hydroxy groups

Article abstract of DOI:10.1016/S0040-4039(00)75823-0

Stereoselective glycosidation of lipid hydroxy groups has been achieved using 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glycosyl chloride as the glycosyl donor in CH₂C1₂. In the presence of ZnCl₂ (1 equiv.) and various "promoters" (1 equiv.) such as Ph₃CCl, 18-crown-6/KCl, n-Bu₄NBr, or Me₃SiCl, β-glycolipid conjugates are formed as the initial products, but they undergo anomerization on prolonged reaction times. The promoters may enhance the solubility of ZnCl₂ in CH₂C1₂.