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A new method for the stereoselective synthesis of alpha- and beta-glycosylamines using the Burgess reagent.

Journal of the American Chemical Society (2004-05-20)
K C Nicolaou, Scott A Snyder, Annie Z Nalbandian, Deborah A Longbottom
RESUMEN

Although glycosylamines constitute an important group of carbohydrates from the standpoint of biology and medicine, methods for their synthesis typically lack substrate generality and/or result in variable stereoselectivity, especially in complex contexts. In this communication, we report an operationally simple method for the synthesis of both alpha- and beta-glycosylamines using the Burgess reagent that overcomes many of these limitations in a bare minimum of synthetic steps.

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(Methoxycarbonylsulfamoyl)triethylammonium hydroxide, inner salt, 97%