An efficient synthesis of N-allylglycosylamides from unprotected carbohydrates
Synthetic, multivalent, carbohydrato assemblies are important tools in studying the avidity of many naturally occuring lectins for their ligands. This report details a simple, high-yielding three-step procedure to convert unprotected carbohydrates into N-allylglycosides. This method compliments the reductive amination procedure but allows the reducing-end pyranose ring to remain intact. No carbohydrate protecting groups are needed, and the resulting N-allylglycosylamide can be easily linked to other molecules. Two examples of analogs of silyl Lewis(x) and sulfo Lewis(X) have been derivatized by this process.
Spevak, Wayne,Dasgupta, Falguni,Hobbs, Christopher J.,Nagy, Jon O.
Synthesis and psychotropic activity of some glycosylamines
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Slivkin,Lapenko,Suntsova,Bykov
p. 235 - 237
(2007/10/03)
A new class of nitrosoureas. II. Synthesis and antitumor activity of 1-(2-chloroethyl)-3,3-disubstituted-1-nitrosoureas having a glucopyranosyl, mannopyranosyl or galactopyranosyl moiety