ACTION OF DIAZOMETHANE ON RIBONUCLEOSIDES - PREPARATION OF RIBONUCLEOSIDE 2'- AND 3'-METHYL ETHERS

Under the conditions described by Broom and Robins (Broom, A. D., and Robins, R. K. (1965), J. Am. Chem. Soc. 87, 1145) both adenosine and cyti-dine were reacted with diazomethane to give ca. three parts of their 2′- to one part of their 3′-O-methyl derivatives. 2′- and 3′-O-methyluridines have been prepared by deamination of the corresponding cytidine deriva tives. The orientations of the 2′- and 3′-methyl ethers of all three nucleosides have been established by nuclear magnetic resonance spectroscopy; the orientations of the uridine derivatives have been confirmed by a chemical method. The stabilities of the glycosidic bonds of adenosine and its 2′- and 3′-methyl ethers are compared. © 1968, American Chemical Society. All rights reserved.