Figure 8: Preparation of Subset A derivatives: introduction of C24 linear and C25 branched aliphatic side chains on hyodeoxycholane scaffold. | Scientific Reports

Figure 8: Preparation of Subset A derivatives: introduction of C24 linear and C25 branched aliphatic side chains on hyodeoxycholane scaffold.

From: Hyodeoxycholic acid derivatives as liver X receptor α and G-protein-coupled bile acid receptor agonists

Figure 8

Reagents and conditions: (a) 2,6-lutidine, t-butyldimethylsilyltrifluoromethanesulfonate, CH2Cl2, 0 °C; (b) LiBH4, MeOH dry in THF dry; (c) DMSO, oxalyl chloride, TEA dry, CH2Cl2, −78 °C, 94% over three steps; (d) n-BuLi, isopropyl triphenylphosphonium iodide, THF dry, r.t.; (e) HCl 37%, MeOH, 80% over two steps; (f) H2, Pd(OH)2 degussa type, THF/MeOH 1:1, 90%; (g) n-BuLi, methyl triphenylphosphonium iodide, THF dry; (h) HCl 37%, MeOH, 95% over two steps; (i) H2, Pd(OH)2 degussa type, THF/MeOH dry 1:1, 88%.

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