Pyridine → HCID 86634143, compound

Participants

Reaction Steps

A solution of allyl α,β-D-ribofuranoside 1 (18.6 g) in dry pyridine (100 mL) was cooled in an ice bath and p toluenesulfonyl chloride (22.4 g, 1.2 eq) was added portion-wise keeping the reaction temperature <5° C. The resulting solution was allowed to warm slowly to RT overnight and then was concentrated to dryness. 1,4-Dioxane (100 mL) was added to the residue and it was again concentrated to dryness. Chromatography of the residue afforded an anomeric mixture of the title compounds 3 as a syrup (17.6 g, 52%). 1H NMR (CDCl3) δ 7.80 (2H, d, J=8.3 Hz), 7.34 (2H, d, J=8.0 Hz), 5.85-5.72 (1H, m), 5.25-5.11 (2H, m), 4.94 (1H, s), 4.27-3.98 (6H, m), 3.87-3.80 (1H, m), 2.44 (3H, s); 13C NMR δ 145.5, 134.1, 133.0, 130.3, 128.4, 117.9, 106.6, 80.8, 75.2, 72.3, 71.0, 68.6, 22.0.

Provenance & Evidence