709032-88-2Relevant academic research and scientific papers
A new method for the stereoselective synthesis of α- and β-glycosylamines using the Burgess reagent
Nicolaou,Snyder, Scott A.,Nalbandian, Annie Z.,Longbottom, Deborah A.
, p. 6234 - 6235 (2004)
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
New uses for the Burgess reagent in chemical synthesis: Methods for the facile and stereoselective formation of sulfamidates, glycosylamines, and sulfamides
Nicolaou,Snyder, Scott A.,Longbottom, Deborah A.,Nalbandian, Annie Z.,Huang, Xianhai
, p. 5581 - 5606 (2007/10/03)
Although the Burgess reagent (methoxycarbonylsulfamoyltriethylammonium hydroxide, inner salt) has found significant use in chemical synthesis as a dehydrating agent, almost no work has been directed towards its potential in other synthetic applications. As this article will detail, we have found that the Burgess reagent is remarkably effective at accomplishing a number of non-dehydrative synthetic tasks when applied to appropriate substrates, such as the formation of sulfamidates from 1,2-diols or epoxyalcohols, α- and β-glycosylamines from carbohydrates, and cyclic sulfamides from 1,2-aminoalcohols. Beyond delineating the power of these new reaction manifolds, we also describe the construction of a group of alternative Burgess-type reagents that extends the scope of these new reactions even further.
Immunostimulatory and antitumor activities of monoglycosylceramides having various sugar moieties
Motoki,Morita,Kobayashi,Uchida,Akimoto,Fukushima,Koezuka
, p. 1487 - 1491 (2007/10/03)
Ten kinds of monoglycosylceramides (MonoCers), having the same ceramide portion and different sugar moieties, were synthesized and their immunostimulatory and antitumor activities were examined. The manner of combination between sugar and ceramide has been demonstrated to affect the manifestation of immunostimulatory and resultant antitumor activities of MonoCers, and in the case of D-MonoCers having the D-sugar, α-D-MonoCers (sugar combined to ceramide in an α-configuration) show stronger activities than β-D-MonoCers. Furthermore, the form of sugar, not the furanose-form but the pyranose-form, and the 2- and 4-hydroxyl groups of the pyranose-form of sugar, seemed to play an important role in the manifestation of the activities of α-D-MonoCers.
