Sodium Azide → HCID 178476366, compound

Participants

Reaction Steps

3,6-tri-O-Acetyl-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-α-D-glucopyranosyl bromide (3) (150 g, 0.282 mol) is suspended in ethyl acetate (3 L) and a solution of 10% aqueous sodium hydrogen carbonate (1500 mL) containing sodium azide (22 g, 0.338 mol) is added. Tetrabutylammonium hydrogen sulfate (28.7 g, 30 mol %) was added and the biphasic mixture stirred vigorously for 16 h. The organic layer was then separated, extracted and dried, then the solvent removed at reduced pressure. The residue was chromatographed as above to yield the desired product (105 g, 75%). 1H NMR (500 MHz, CDCl3) δ 13.90 (d, J=9.6, 1H), 5.22 (t, J=9.6, 1H), 5.11 (t, J=9.7, 1H), 4.90 (d, J=8.9, 1H), 4.36 (dd, J=4.5, 12.5, 1H), 4.17 (dd, J=12.4, 1.7, 1H), 3.81-3.91 (m, 2H), 2.60 (s, 3H), 2.42 (s, 2H), 2.36 (s, 2H), 2.11, (s, 3H), 2.04 (s, 3H), 1.03 (s, 3H) M/z 495 (M+H).

Provenance & Evidence