Diisopropylethylamine → 2-Deoxyglucose

Participants

Reaction Steps

D-Glucosamine hydrochloride (13 mg, 0.06 mmol) was added to a solution containing sodium methoxide (3.24 mg, 0.06 mmol) in 3 mL DMSO. The reaction mixture was stirred at room temperature for 2 hrs, and purpurin-18-N-3′-(isothiocyanate)propylimide (19 mg, 0.028 mmol) and 50 μL diisopropylethylamine were added. The resulting solution was stirred under argon atmosphere for 20 hrs. After removing solvent and base by vacuum, the crude obtained was washed with both CH2Cl2 and, water and subsequently crystallized from MeOH. The desired 2-deoxyglucose conjugate (5) was obtained (8 mg). The filtrate was further concentrated and purified by silica gel plate chromatography (10% MeOH in CH2Cl2) to yield 4 mg of product. Thus, the total yield for 5 was 50% (12 mg). UV-vis in DMSO λmax: 366 nm (ε: 5.3×105), 419 (1.4×104), 550 (2.4×104), 648 (8.0×103) and 705 (5.2×104). Mass calcd for C44H53N7O9S: 878.3523 (M+Na)+; found by HRMS; 878.3542 (M+Na)+. 1H NMR (DMSO-d-6, δ ppm): 9.27, 9.16 and 8.85 (each s, 1H, for 10, 5 and 20-H), 8.01 (dd, 1H), 7.80 (br, 1H), 6.55 (br, 1H), 6.33 (d, 1H), 6.12 (d, 1H), 5.24-4.21 (9H), 3.80-3.40 (13H), 2.90 (s, 3H), 2.60 (m, 1H), 2.50-2.30 (m, 2H), 2.08 (m, 2H), 1.8 (m, 1H), 1.72 (d, 3H), 1.41 (t, 3H), −0.61 and −0.67 (each s, 1H, 2×NH).

Provenance & Evidence