1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxyhexopyranose → HCID 21967595, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-azido glucose tetraacetate 57 (0.222 g, 0.59 mmol) in 6.6 mL of CH2Cl2 is added 4-hydroxythiophenol (0.146 g, 1.15 mmol) followed by boron trifluoride diethyl ether complex (15.9 mL, 18.4 g. 141 mmol). The reaction mixture is heated at 45° C. for 12 h and then quenched by the addition of 2 mL of H2O. The reaction mixture is diluted with 25 mL of CH2Cl2, washed with H2O (10 mL), saturated NaCl (10 mL), dried over Na2SO4, filtered, and concentrated to afford 0.232 g of crude 2-azido-1,2-dideoxy-1-(4-hydroxyphenylthio)-3,4,6-tri-O-acetyl-α,β-D-glucopyranose 58 as a yellow oil, a mixture of anomers which is then taken on to the next step without further purification.

Provenance & Evidence