Synthesis of peptidomimetics based on iminosugar and β-d-glucopyranoside scaffolds and inhibiton of HIV-protease

Synthesis of α‐Acyloxynitrones and Reactivity towards Samarium Diiodide

“…Free hydroxy groups were protected as benzyl ethers, the second isopropylidene group was hydrolyzed in aqueous acetic acid at 110 °C, and 12 was then obtained by easy acylation of the C‐1 primary OH group with pivaloyl chloride . Formation of the protected oxime at C‐2, was effected by treating 12 with O ‐( tert ‐butyldimethylsilyl)hydroxylamine in the presence of a catalytic amount of pyridinium para ‐toluenesulfonate under dehydrating conditions at 110 °C for 20 h. The primary alcohol at C‐6 was then converted into a leaving group by mesylation, prior to treatment with silica‐supported tetrabutylammonium fluoride.…”

Synthesis of Somatostatin Mimetics Based on 1‐Deoxynojirimycin

“…(8). Compound 7 [20,24] (550 mg, 1.85 mmol) was dissolved in anhyd pyridine (4 mL) and DMAP (226 mg) was added. The mixture was cooled to 0 8C and MMTrCl (687 mg, 2.22 mmol) in anhyd pyridine (4 mL) was added dropwise.…”

“…The synthesis of both 5 and 6 commenced from DNJ 3 which was first prepared as previously described [19] from l-sorbose and then 3 was converted into the CBz derivative 7 [20] as outlined previously. The reaction of 7 with monomethoxytrityl chloride in pyridine in the presence of DMAP followed by benzylation of the tritylated intermediate gave 8 (62 % over two steps; see Scheme 1).…”

Carbohydrates as Scaffolds in Drug Discovery

“…Out of several mannose and glucose derivatives, 22 proved to be the most active, with an IC 50 value of 3.81 μ M . Introduction of side chains (as in compound 23 ) to pick up additional hydrogen bonds in the binding site did not lead to an improvement in binding affinity45 (Figure 9).…”