6-AMINO-6-DEOXY-D-GLUCOSE HYDROCHLORIDE synthesis

Yield:4460-60-0 89%

Reaction Conditions:

Stage #1: 6-Azido-6-desoxy-D-glucopyranosewith hydrogen;palladium 10% on activated carbon in methanol;water at 20; under 1551.49 Torr;
Stage #2: with hydrogenchloride

Steps:

7

3 (0.5 g, 2.44 mmol) was dissolved in 120 mL of MeOH-H₂O (1:1), Pd/C (10%, 150 mg) was added, and the mixture was subjected to 30 psi of hydrogen at room temperature for 30 h. After removal of the catalyst by filtration, the solution was evaporated in vacuo to give colorless solid (0.47 g, 89%): mp 139141° C.; TLC (SiO₂) R_f 0.26 (eluants 7:2:2 isopropanol-water-ammonia water); ¹H-NMR (D₂O, 300 MHz) δ 5.13 (d, J_1,2=3.66 Hz, 1H, H-1α), 4.55 (d, J_1,2=7.94 Hz, 1H, H-1β); ¹³C-NMR (DMSO-d₆, 75 MHz) δ 97.1(C-1β), 92.4(C-1α), 76.1(C-3β), 74.6(C-3α), 72.4, 72.1, 71.9, 71.7(C-2α, 2β, 5α, 6β), 71.4(C-4β), 67.5(C-4α), 40.3 (C-6α, 6β).

References:

US2007/21380,2007,A1 Location in patent:Page/Page column 13