Synthesis of stereospecifically labeled 3,6-dideoxyhexoses

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Preparations of ascarylose (3,6-dideoxy- l- arabino-hexose), abequose (3,6-dideoxy- d- xylo-hexose), and paratose (3,6-dideoxy- d- ribo-hexose) with stereospecific deuterium labeling at C-3 are discussed. The methods used to synthesize these sugars, such as the hydrogenation of olefins, the displacement of halides, the reduction of epoxides, and the substitution of tosyl esters, illustrate a variety of strategies leading to stereospecific deuterium incorporation. Many of the techniques described here should be of general utility for the synthesis of other deuterium-labeled sugars.