With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10534-59-5,Tetrabutylammonium acetate,as a common compound, the synthetic route is as follows.
To a solution of benzyl (2-((((3,5-bis(trifluoromethyl)sulfonyl)oxy)-4,6-di-O- benzoyl-beta-D galactopyranosyl)oxy)ethyl)carbamate (16.9 g, 20.37 mmol) in anhydrous toluene (100 mL), was added a solution of tetra butylammonium acetate (25 g, 82.9 mmol) in a mixture of toluene (150 mL) and DMF (4 mL) was added and the resulting mixture stirred at room temperature overnight. Diluted with of CH2Cl2 (30 mL) and washed with sat. NaCl (2 x 100mL), dried over MgSO4, filtered and evaporated. The residue was purified by silica gel column chromatography (Teledyne Isco : 330g) eluent: 0-50% EtOAc / Hexane (10cv) then 50% EtOAc / Hexane (5cv) to give the title compound (8 g, 60.5%).1H NMR (CDCl3) delta 8.10 (2H, m), 7.98 (2H, dd, J = 8.1 and 1.4 Hz), 7.61 (2H, m), 7.48 (2H, t, J = 7.8 Hz), 7.46 (2H, t, J = 7.7 Hz), 7.37 (4H, m), 7.33 (1H, m), 5.70 (1H, d, J = 3.3 Hz), 5.61 (1H, t, J = 10.0 Hz), 5.29 (1H, dd, J = 10.0 and 3.3 Hz), 5.26 (1H, m), 5.10 (2H, s), 4.79 (1H, s), 4.64 (1H, dd, J = 12.1 and 2.7 Hz), 4.47 (1H, dd, J = 12.1 and 5.8 Hz), 3.94 (2H, m), 3.74 (1H, m), 3.48 (1H, m), 3.37 (1H, m), 2.15 (3H, s), 2.00 (3H, s).
As the paragraph descriping shows that 10534-59-5 is playing an increasingly important role.
Reference£º
Patent; MERCK SHARP & DOHME CORP.; FENG, Danqing; GUIDRY, Erin, N.; HUO, Pei; KAARSHOLM, Niels, C.; LIN, Songnian; NARGUND, Ravi, P.; YAN, Lin; (233 pag.)WO2016/164288; (2016); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI