Fig. 3: The reaction scope of various glycosyl donors.
From: Stereoselective gold(I)-catalyzed approach to the synthesis of complex α-glycosyl phosphosaccharides

aTemperature: 0 °C, 30 min then 60 °C, 2 h. bTemperature: 0 °C, 30 min, then 20 °C, 2 h. cTemperature: 0 °C, 30 min, then 100 °C, 2 h. dgalactosyl trichloroacetimidate was used as donor in the presence of TMSOTf (0.1 equiv.) at 0 °C in 30 min. eOn 1.2 g scale with 0.5 mol% Ph3PAuNTf2. f0.2 equiv. of i-Pr2NEt was used as additive. gYields of α/β mixtures (α/β mixtures were not separable, except 3e and 3i), and ratios were determined by crude 31P NMR. Bn: benzyl. Bz: benzoyl. Ph: phenyl. Ac: acetyl. Tf: trifluoromethanesulfonyl. In red are the formed glycosidic bonds. In blue are the acceptors of phosphoric acids and the phosphate moieties in the products.