The general procedure for the synthesis of (2S,3R,4S,5S,6R)-6-((triphenylmethoxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetraol from D-anhydrous glucose and triphenylmethyl chloride was as follows: D-anhydrous glucose (5 g; 0.0277 mol) was suspended in pyridine (50 mL), followed by addition of triphenylmethyl chloride. The reaction mixture was stirred at 80 °C for about 4 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) using dichloromethane: methanol (85:15) as the unfolding agent. Upon completion of the reaction, the reaction was quenched with water (100 mL) and extracted with dichloromethane (150 mL x 2). The organic layers were combined, washed with saturated aqueous sodium bicarbonate and dried over anhydrous sodium sulfate. The solvent was subsequently removed using a rotary evaporator. The target product (2S,3R,4S,5S,6R)-6-((triphenylmethoxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetraol (10.3 g; 88% yield) was finally obtained by milling the crude product with a hexane:ether mixture (100 mL) to remove residual triphthaloyl chloride and pyridine. The structure of the product was confirmed by LC-MS and the molecular ion peak (M+) was observed to be 446 amu.
