反应详情

0.52 g (3.0 mmole) of 1,5-anhydro-2-azido-2,3-dideoxy-D-glucitol (11) were dissolved in 9 ml of pyridine. Thereafter, 1.1 g (3.2 mmole) of 4,4′-dimethoxytritylchloride in 9 ml of pyridine are added at r.t. within 30 min under stirring. The reaction mixture was stirred for another 3 h at r.t. Then pyridine was evaporated and the residue was dissolved in 100 ml of ethyl acetate und washed twice with 60 ml of 5% sodium hydrogencarbonate solution. Organic layer was separated, dried over sodium sulfate, filtered and evaporated to dryness. The residue was dissolved in 5 ml of ethyl acetate and purified by flash-chromatography over silica gel (n-hexane/ethyl acetate/1% triethylamine gradient). Product fractions were combined, evaporated and dried at high vacuum to yield 1.1 g (77%) of a colorless foam.

1. stirringThe reaction mixture was stirred for another 3 h at r.t
2. customThen pyridine was evaporated
3. dissolutionthe residue was dissolved in 100 ml of ethyl acetate
4. washund washed twice with 60 ml of 5% sodium hydrogencarbonate solution
5. customOrganic layer was separated
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customevaporated to dryness
9. dissolutionThe residue was dissolved in 5 ml of ethyl acetate
10. custompurified by flash-chromatography over silica gel (n-hexane/ethyl acetate/1% triethylamine gradient)
11. customevaporated
12. customdried at high vacuum