Magnesium Perchlorate: Highly Efficient and Versatile Catalyst for the Ferrier Glycosylation Reaction

Recent Developments in the Ferrier Rearrangement

“…In addition, economically convenient catalysts such as Fe 2 (SO 4 ) 3 · x H 2 O85 and Mg(ClO 4 ) 2 ,86 the former under microwave irradiation conditions, have emerged as alternative Lewis acids in the Ferrier rearrangement of 3,4,6‐tri‐ O ‐acetyl‐ D ‐glucal ( 5 , Table 7).…”

Palladium catalyzed reactions on glycal scaffolds : syntheses of glycal derivatives and C-glycosides

“…Amongst C2 functionalized glycals, formation of diene moiety (Figure 1.3) by attaching another alkene molecule has become increasingly promising because the diene can potentially serve as ideal building block to bicyclic natural products, such as Olivin, 10 Forslolin 11 and Jamesoniellede 12 by Diels-Alder cyclization (Figure 1.4). 13 In the past decade, palladium catalyzed alkene-alkene direct coupling have attracted considerable attention. 14 17 Another C-H alkenylation example using tetrahydronpyrido [1,2a]pyrimidines and olefins was published in 2009 by Gallagher's group.…”

“…After the optimal reaction conditions were determined, we proceeded to explore the substrate scope of the glycal part and the results were summarized in Table 3.4. The protecting group studies showed that the desired C-glycosides were formed only when the C-3 protecting groups were acetyl (7,9,11,13,15) or ethoxycarbonyloxyl (17). Glycals with other C3 protecting groups such as TMS and TBS, as well as the acid tolerant benzyl and benzoyl groups, failed to provide any product.…”

“…J = 2.0, 7.2, 10.3, 1H), 5.92 (ddd, J = 1.3, 2.7, 10.3 Hz, 1H);13 C NMR (CDCl 3 , 100 MHz) δ17.4, 21.2, 22.3, 22.7, 25.1, 25.8, 67.7, 70.2, 74.8, 124.0, …”

“…1H), 3.91-3.94 (m, 0.64H), 3.78-3.82 (m, 1H), 2.11 (s, 1.77H), 2.09 (s, 3H), 2.08 (s, 1.68H), 2.08 (s, 3H);13 C NMR (CDCl 3 , 100 MHz) δ 171.…”