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Triazine Derivative Usable for the Glycosylation of Unprotected Sugars
Advantages
- The synthesis of unprotected glycosyl donors can be performed.
- The reaction proceeds under basic conditions.
- Also applicable to unprotected polysaccharides.
Application
Experimental procedure:
B4587 (12.3 g, 37.5 mmol) is added to a solution of D-glucose (4.5 g, 25 mmol), N-methylmorpholine (4.1 mL, 38 mmol) and ammonia (3.3 mL, 50 mmol, 29% aqueous solution) in the mixture of acetonitrile and water (125 mL, CH3CN:H2O = 1:1) and the resulting mixture is stirred for 3 h at 0 °C. After concentration in vacuo, the residue is washed with water and chloroform. The filtrate is concentrated in vacuo to give β-glucoside (9.42 g, 20.0 mmol, 80 % yield).
Excess amount of alcohol is added to the mixture of β-glucoside (0.2 mmol) and Pd/C (5 mg). Under hydrogen atmosphere, the resulting mixture is stirred at room temperature. The reaction mixture is filtered, and the filtrate is concentrated in vacuo to afford the alkoxy group substituted glucosides.
References
- Protection-free Synthesis of Alkyl Glycosides under Hydrogenolytic Conditions
