Abstract
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 CH 2Cl 2. In the presence of ZnCl 2 (1 equiv.) and various “promoters” (1 equiv.) such as Ph 3CCl, 18-crown-6/KCl, n-Bu 4NBr, or Me 3SiCl, β-glycolipid conjugates are formed as the initial products, but they undergo anomerization on prolonged reaction times. The promoters may enhance the solubility of ZnCl 2 in CH 2Cl 2.
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