Synthesis of the phosphoramidite derivative of 2'-deoxy-2'-C-beta-methylcytidine.
2'-Deoxy-2'-C-beta-methylnucleosides elicit interest as potential therapeutic agents and as analogues for the analysis of nucleic acid structure and function. An efficient route for the synthesis of 2'-deoxy-2'-C-methyluridine (11), 2'-deoxy-2'-C-methylcytidine (12), and the phosphoramidite derivative of 2'-deoxy-2'-C-beta-methylcytidine (10, 46% overall yield) from 1,2,3,5-tetra-O-benzoyl-2-C-beta-methylribofuranose (1) is described.
Li
Nan-Sheng
NS
Howard Hughes Medical Institute, Department of Biochemistry and Molecular Biology, University of Chicago, 5841 South Maryland Avenue, MC 1028, Chicago, Illinois 60637, USA.
Piccirilli
Joseph A
JA
D003562:Cytidine / Q000031:analogs & derivatives; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D014529:Uridine / Q000031:analogs & derivatives
D007202:Indicators and Reagents; D003841:Deoxycytidine; C055031:2'-methyl-2'-deoxycytidine; D003562:Cytidine; D014529:Uridine