Stereoselective synthesis of [5'-2H1][5'-13C]nucleosides.
An approach to a synthesis of stereoselective 5'-monodeuterated nucleoside combined with 13C label is described. A preparation of (5R)-D-[5-(2)H1;5-(13)C]ribose derivative of 1,2:5,6-di-O-isopropyliden-alpha-D-allofranose was successfully achieved by a 13C Wittig reaction using Ph3P13CH3I-BuLi to 5-oxoribose derivative and subsequent transformation into D-[5-(13)C]ribose derivative with an AD reaction, selective acylation, oxidation with NaIO4, and a stereoselective deuteride transfer reaction from Alpine-Borane-d to 5-oxo-D-[5-(13)C]ribose derivative as the main reaction. (5'R)-[5'-(2)H1;5'-(13)C]nucleosides were synthesized in the established manner from this 5-(13)C/2H1-double-labeled ribose.
Kinugawa
Yoshinobu
Y
Laboratory of Pharmaceutical Chemistry, School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1, Horinouchi, Hachioji, Tokyo, 192-0392, Japan.
Kawashima
Etsuko
E
D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D009705:Nucleosides