反应详情

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).

1. stirringthe mixture was stirred for one hour
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationAfter filtration
6. concentrationthe filtrate was concentrated
7. customThe residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)