Synthesis of N-Glucosyl Ethyl and Butyl Phosphoramidates

The Staudinger-phosphite reaction has found extensive use in diverse biological applications. A subset of this reaction has been employed in the synthesis of glycosyl phosphoramidates, either conjugated to peptides and proteins or as stand-alone derivatives, which have been proposed as useful building blocks for drug development. All chemicals used were reagent grade and used as purchased, unless otherwise stated. Reaction mixtures were stirred magnetically. Combustion analysis was performed with a PerkinElmer 2400 Series II CHNS/O. The solution was stirred at room temperature and the reaction was monitored by TLC. When the starting material was consumed, the mixture was concentrated in vacuo, diluted with CH2Cl2 and washed with water.