2,3,4-TRI-O-ACETYL-ALPHA-L-ARABINOPYRANOSYL BROMIDE synthesis

Yield:75247-31-3 53%

Reaction Conditions:

with hydrogen bromide;acetic acid in dichloromethane at 0 - 20; for 3 h;

Steps:

General procedure for the bromination A2

General procedure: HBr (33 % wt in acetic acid) was added dropwise to a cooled solution (0 °C) of the peracetylated saccharide in dichloromethane (10 mL) and stirred for 3 h at rt. Ice water (50 mL) was added to the mixture and the aqueous phase was extracted with dichloromethane (3 x 50 mL). The combined organic layers were washed with 0.5 % Na₂S₂O₃ (1 x 75 mL), sat. NaHCO₃ (3 x 75 mL), brine (1 x 75 mL) and dried over Na₂SO₄. The solvent was evaporated under reduced pressure and the crude product crystallized from diethylether/pentane to afford the halogenated substrate.

References:

Bachmann, Thomas;Schnurr, Christian;Zainer, Laura;Rychlik, Michael [Carbohydrate Research,2020,vol. 489,art. no. 107940] Location in patent:supporting information