Glycosyl azides synthesis

Ferndndez-Bolanos JG, Lopez 6 (2007) Synthesis of Heterocycles from Glycosylamines and Glycosyl Azides. 7 31-66... 

Scheme 21. Synthesis of mannosylated fulleroglyco hybrids by [3+2]-cycloaddition of glycosyl azide...

Scheme 36 Synthesis of the Pentasaccharide Core as the Glycosyl Azide from Glycal Precursors13931...

Fig. 11. Synthesis of glycosyl amine by reduction of glycosyl azide (88,95).

Tropper, F Andersson, F., Braun, S., and Roy, R. (1992) Phase transfer catalysis as a general and stereoselective entry into glycosyl azides from glycosyl halides. Synthesis 618-620. 

Malkinson, J. P., Falconer, R. A., and Toth, 1. (2000) Synthesis of C-terminal glycopeptides from resin-bound glycosyl azides via a modified Staudinger reaction. J. Org. Chem. 65, 5249-5252. 

The base-catalyzed condensation of azides with activated methylene compounds is a well-established route to 1/7-triazoles. This is a regiospecific method ideally suited for the synthesis of triazoles with a 5-amino or -hydroxy substituent, and an aryl or carbonyl function at C-4. The general scheme is shown in Scheme 8. The stepwise character of the reaction is best revealed by the anomerism of glycosyl azides during their reaction with... 

A-Glycosyl-1,2,3-triazoles, obtainable from glycosyl azides, were used for glycoside synthesis in TMSOTf-promoted reactions [577]. Thus, the reaction of 263 with carminomycinone 264 produced the glycoside 265 in excellent yield [577] (Scheme 4.51). 

Maunier, V, Boullanger, P, Lafont, D, A one-pot synthesis of glycosyl amides from glycosyl azides using a modified Staudinger reaction, J. Carbohydr. Chem., 16, 231-235, 1997. 

Scheme 1 (a) Synthesis of glycosyl azide, (b) Reduction of glycosyl azide to the corresponding glycosylamine followed... 

Another method for the synthesis of glycosyl fluorides consists of 1,3-dipolar cycloaddition of glycosyl azides with di-f-butyl acetylenedicarboxylate and subsequent treatment of the triazole derivatives with HF-pyridine. ... 

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