Uses
1,2,3,4,6-PENTA-O-ACETYL-ALPHA-D-MANNOPYRANOSE was used for glycosylation in a study that assessed novel synthetic inhibitors of selectin-mediated cell adhesion. 1 It has also been used in a study to investigate stereospecific entry to spiroketal glycosides using alkylidenecarbene CH insertion.
Uses
1,2,3,4,6-Penta-O-acetyl-α-D-mannopyranose (cas# 4163-65-9) is a compound useful in organic synthesis.
Synthesis
D-Anhydrous glucose (3.00 g, 16.6 mmol) was dissolved in anhydrous pyridine (33 mL) and acetic anhydride (31.5 mL, 333 mmol) was added slowly and dropwise at 0 °C and under nitrogen protection. The reaction mixture was stirred at 0 °C for 1 h. After that, a catalytic amount of DMAP (200 mg, 1.67 mmol) was added. Subsequently, the reaction mixture was gradually warmed up to room temperature, during which a slight exothermic phenomenon was observed. After 6 hours of reaction, the clarified yellow reaction solution was slowly poured into rapidly stirred ice water (125 mL) and a viscous solid was precipitated. After extraction by ethyl acetate (345 mL), the solvent was evaporated and co-evaporated with anhydrous toluene (320 mL) to give the final fully acetylated glucose as a yellow solid (5.84 g, 90% yield).
References
[1] Angewandte Chemie, International Edition, 2009, vol. 48, p. 2723 - 2726
[2] Angewandte Chemie, 2009, vol. 121, p. 2761 - 2764
[3] Tetrahedron, 2013, vol. 69, # 41, p. 8731 - 8737
[4] Green Chemistry, 2011, vol. 13, # 1, p. 59 - 63
[5] Journal of the Chinese Chemical Society, 2009, vol. 56, # 2, p. 398 - 403
