Synthesis
GENERAL STEPS: To a solution of 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-D-glucopyranose hydrochloride (19.8 g, 67 mmol) in pyridine (130 mL) was added ethanoic anhydride (70 mL). The reaction mixture was stirred at room temperature overnight and subsequently concentrated under reduced pressure to afford (2S,3R,4R,5R,6R)-3-acetamido-6-(acetyloxymethyl)tetrahydro-2H-pyran-2,4,5-triacetic acid tris ester as a crude product as a yellow solid, which could be used in the next reaction without further purification. The above crude product (12 g, 26 mmol) was dissolved in acetone (130 mL) and aqueous hydrochloric acid (6.6 mL, 5N) was added slowly and dropwise at 0 °C. The reaction mixture was continued to be stirred at 0 °C for 1 h. The precipitate was subsequently removed by filtration. The filter cake was dried to give the target product as a white solid (7.50 g, 75% yield).
References
[1] European Journal of Organic Chemistry, 2012, # 9, p. 1699 - 1702
[2] Carbohydrate Research, 2015, vol. 413, p. 135 - 144
[3] Journal of Organic Chemistry, 1954, vol. 19, p. 1793,1798
[4] Chemische Berichte, 1931, vol. 64, p. 975,978
[5] Carbohydrate research, 1985, vol. 136, p. 309 - 323
