Tritylation, of carbohydrates

Because carbohydrates are so frequently used as substrates in kinetic studies of enzymes and metabolic pathways, we refer the reader to the following topics in Ro-byt s excellent account of chemical reactions used to modify carbohydrates formation of carbohydrate esters, pp. 77-81 sulfonic acid esters, pp. 81-83 ethers [methyl, p. 83 trityl, pp. 83-84 benzyl, pp. 84-85 trialkyl silyl, p. 85] acetals and ketals, pp. 85-92 modifications at C-1 [reduction of aldehydes and ketones, pp. 92-93 reduction of thioacetals, p. 93 oxidation, pp. 93-94 chain elongation, pp. 94-98 chain length reduction, pp. 98-99 substitution at the reducing carbon atom, pp. 99-103 formation of gycosides, pp. 103-105 formation of glycosidic linkages between monosaccharide residues, 105-108] modifications at C-2, pp. 108-113 modifications at C-3, pp. 113-120 modifications at C-4, pp. 121-124 modifications at C-5, pp. 125-128 modifications at C-6 in hexopy-ranoses, pp. 128-134. 

The application of tritylpyridinium tetrafluoroborate, easily obtained from trityl tetrafluoroborate and pyridine, presents definitive advantages [319, 320] over the classical procedure discussed in the previous section. Acetonitrile solvent simplifies the workup procedure, the substantially shorter reaction times enable the use of only a slight excess of the reagent. Preferential tritylation of the primary hydroxyl group in carbohydrates is especially convenient with this method. 

Y. V. Vozney and N. K. Kochetkov, Tritylation of secondary hydroxyl groups of sugars by triphenylmethylium salts, Carbohydr. Res., 54 (1977) 300-303. 

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