Abstract
Nucleophilic addition (Nu −M +) to isolevoglucosenone 1 generates enolates stereospecifically ( exo face addition) that can be reacted with sugar-derived aldehydes to give C(1→3)-linked disaccharide precursors with high diastereoselectivity. Limitations of the method arising from unfavorable aldolate stability can be overcome by using Et 2AlI as the nucleophile. This leads to products of Baylis–Hillmann condensations. One example is presented and has led to the preparation of 2,3-anhydro-3- C-[(1 S)-2,6-anhydro- d -glycero- d- gulo-heptitol-1- C-yl]-β- d- gulo-pyranose 5.
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