A systematic approach, which combines previously reported reactions with appropriate modifications, was established for preparing a variety of selectively deuterated nucleosides from glucose. We have developed a systematic method of synthesizing specifically deuterated nucleosides from glucose. Selectively C-13/H-2-doubly labeled nucleosides, such as [1',2',3',4',5'-C-13(5);3',5'-H-2(2)]- and [1',2',3',4',5'-C-13(5);4',5'-H-2(2)]-adenosines, have been synthesized starting from [ul-C-13(6)]-D-glucose. These labeled nucleosides are very useful for precise conformational analyses of nucleic acids in solution by heteronuclear multidimensional NMR spectroscopy. (C) 1998 Elsevier Science Ltd. All rights reserved.