Synthesis of pseudo-C-nucleosides

Synthesis of new isoxazoles derivatives attached to sugar moieties

“…These formyl-compounds were prepared in several steps from D-glucose, D-allose and D-galactose. Compounds 1 and 2 were obtained by oxidative cleavage of the corresponding diol derivatives with NaIO 4 [18,19]. The synthesis of compound 3 has been reported by several methods [20,21], but in this sequence the 6-OH oxidation of the commercially available 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose was performed with PCC and molecular sieves, in 73% yield.…”

Synthesis and Biological Evaluation of Sugars Containing α,β‐Unsaturated γ‐Lactones

“…3-O-Benzyl-1,2-O-isopropylidene-α--allofuranose [24] (1.00 g, 3.22 mmol) gave 7 (0.595 g, 60 %) as a colorless syrup after after purification by CC (EtOAc/petroleum ether, 2:3). [25] (0.473 g, 1.82 mmol) gave 8 (0.289 g, 61 %) as a colorless oil after purification by CC (EtOAc/cyclohexane, 3:7).…”

Synthesis of a novel uridine analogue and its use in attempts to form new cyclonucleosides using ring-closing metathesis

“…The choice to use 6 as starting material conducted us to invert the configuration of the carbon atom in position 3 (hydroxyl group in  position to  position) to have the D-ribose configuration as natural nucleoside. The well-established protection of 6 followed by successive oxidation, selective reduction to obtain the D-allose derivative [22], benzylation of the hydroxyl group in position 3 [23,24] and deprotection of the diol in position 5,6 [24,25] gave the D-allose derivative 7 in 51% overall yield (five steps). At this step it was notable that the oxidative cleavage followed by addition of the hex-5-ene magnesium bromide could be studied.…”