Methanesulfonyl chloride → 2,3,4,6-Tetra-O-benzyl-1,5-di-O-mesyl-D-glucitol

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Reaction Steps

2,3,4,6-Tetra-O-benzyl-D-glucitol (45 g) was dissolved in pyridine (200 ml) and added over 30 min to a solution of mesyl chloride (15 ml) in pyridine (100 ml) at 0° C. The clear solution was stored at 4° C. overnight, after which time TLC analysis showed completion of the reaction. The reaction mixture was partitioned between ethyl acetate and water/ice. The organic fractions were washed with 5% hydrochloric acid then saturated aqueous sodium bicarbonate solution, dried (Na2SO4) and concentrated to a yellow/orange oil. The oil was azeotroped with toluene and used directly in the next stage.

Provenance & Evidence