Water → N-Acetyl-D-Galactosamine

Participants

Reaction Steps

The above compound was prepared as above using (S)-2-amino-6-(E)-hexadec-8-enoylamino)-hexanoic acid 2-trimethylsilanyl-ethyl ester and cleaving the protecting group as follows: After the penultimate step, the resultant 2-trimethylsilanyl-ethyl ester (245 mg, 0.107 mmol, Eq: 1.00) was combined with THF abs, (5 mL) to give a colorless solution. Tetrabutyl-ammonium fluoride trihydrate (168 mg, 0.533 mmol, Eq: 5.00) was added at 0° C. and the reaction was stored in the fridge over night. Pouring onto crushed ice, extraction with ethyl acetate, washing with water, drying over Na2SO4, and evaporation of all solvents yielded a sticky oil. Dissolution in acetonitrile and water and lyophilization afforded eventually 0.120 g of the title compound as white solid, MS (ISP): 112.5 [M+2Na]2+/2.

Provenance & Evidence