Synthesis of stereospecifically labeled 3,6-dideoxyhexoses.
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.
Department of Chemistry, University of Minnesota, Minneapolis 55455-0431.
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Russell
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Weigel
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Han
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Liu
D002236:Carbohydrate Conformation; D003903:Deuterium; D006601:Hexoses / Q000138:chemical synthesis*; D007553:Isotope Labeling; D009682:Magnetic Resonance Spectroscopy; D012015:Reference Standards; D013237:Stereoisomerism
D006601:Hexoses; C009616:tyvelose; C022880:paratose; C023708:abequose; D003903:Deuterium