Tetrahydrofuran → HCID 69381461, compound

Participants

Reaction Steps

A 1.6 M hexane solution of n-butyl lithium (2.44 ml) was added dropwise to a solution of 2-(3-bromobenzyl)-1-methylazulene (1.2 g) in THF (8.0 ml) at −78° C. and the mixture was stirred for one hour. Then, a solution of 2,3,4,6-tetra-O-benzyl-D-(+)-glucono-1,5-lactone (2.08 g) in THF (8.0 ml) was added dropwise to the reaction mixture and the mixture was stirred for one hour. Saturated aqueous solution of ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain 2,3,4,6-tetra-O-benzyl-1-C-[3-[(3-methylazulen-1-yl)methyl]phenyl]-D-glucopyranose (1.74 g).

Provenance & Evidence