Synthesis of the Phosphoramidite Derivative of 2‘-Deoxy-2‘-C-β-methylcytidine

2‘-Deoxy-2‘-C-β-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...

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Veröffentlicht in:	Journal of organic chemistry 2003-08, Vol.68 (17), p.6799-6802
Hauptverfasser:	Li, Nan-Sheng, Piccirilli, Joseph A
Format:	Artikel
Sprache:	eng
Schlagworte:	Cytidine - analogs & derivatives Deoxycytidine - analogs & derivatives Deoxycytidine - chemical synthesis Deoxycytidine - chemistry Indicators and Reagents Magnetic Resonance Spectroscopy Models, Molecular Uridine - analogs & derivatives
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Beschreibung
Zusammenfassung:	2‘-Deoxy-2‘-C-β-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-β-methylcytidine (10, 46% overall yield) from 1,2,3,5-tetra-O-benzoyl-2-C-β-methylribofuranose (1) is described.
ISSN:	0022-3263 1520-6904
DOI:	10.1021/jo034263y