Carbohydrates, azido-containing

In addition, bifunctionalized carbohydrate derivatives containing simultaneously one azido and alkyne groups have been intermoleculary reacted, affording cyclic carbohydrate-containing molecule of interest that also possess more that one triazole ring in their structures. 

The latter sequence, as reported by Overkleeft, van Boom and coworkers, employs substrates of type 9-42 containing both azide and aldehyde functionalities. Treatment of 9-42 with PMe3 in MeOH at room temperature forms a cyclic imine 9-43 via an intermediate phosphazene. Following the addition of an acid and an isocyanide 9-43, products of type 9-44 are obtained. According to this scheme, enan-tiopure carbohydrate-derived azido aldehydes 9-45 and 9-48 led to the morpholino compounds 9-46 and 9-47, as well as to the pipecolic acid scaffolds 9-49 and 9-50, re-... 

R. D. Guthrie and D. Murphy, Nitrogen-containing carbohydrate derivatives. IV. Azido-and epimino-sugars, J. Chem. Soc. (1963) 5288-5294. 

Azido photochemistry was frequently used to introduce functional groups onto polymeric substrates. It is also the main so-called grafting-to technique usually used to efficiently modify or functionalize surfaces [HAR 91, THO 98, ZIA 99]. This method was employed to covalently graft carbohydrates [KNA 01] or polysaccharides [BAR 01, BHA 08] containing azide groups to polymer substrates and was successfully used to modify a wide range of other substrates such as glass, tin oxide, silicon and aluminum. 

Nitrogen, Sulphur and Selenium-containing Compounds. - The S- and 6-substituted 3-amino-l,2,4-triazines 5 and 6, the spiro-naphthoxazine 7, the hetero Diels-Alder cycloadduct 8, 5-azido-3-0-benzyl-6-0-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-P-L-talofuranose, 9 5-azido-6-0-benzoyl-3,5-dideoxy-3-fluoro-l,2-<9-isopropylidine-a-D-glucofuranose, kedarosamine (2,4-dideoxy-4-dimethylamino-L-fucopyranose) as the 3-0-(4-bromobenzoyl) derivative. 1,2 5,6-Di-0-isopropylidene-a-D-ribohexos-3-ulose phenylhydrazone, p-iactam 9 (from a diastereoselective [2+2] cycloaddition to a carbohydrate-based arylimine), 3 the D-arabino and D-ribo lactam derivatives 10 and 11, " the fully-protected iminosugar 12, 5 2,3,4,5-tetra-0-acetyl-6-amino-6-deoxy-D-mannonolactam, 4,8-anhydro-3-... 

The efficiency of Click coupling reactions was shown by the work of Hawker and coworkers [196] on the synthesis of asymmetric dendrimers from unprotected azido-sugars and aUcyne-terminated dendrimers. The produced materials contained multiple functionalities (carbohydrate and fluorophore). 

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