Chelation-controlled regioselective alkylation of pyrimidine 2'-deoxynucleosides.
Protection-deprotection steps, which are usually needed for regioselective alkylation of pyrimidine deoxynucleosides, can be avoided by choosing the appropriate solvent. The combined effects of low dielectric constant and possible sodium chelation by pyrimidine nucleosides may account for the unexpected regioselectivity observed in THF.
Lucas
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R
Laboratoire de Chimie des Substances Naturelles EA1069, Faculté des Sciences et Techniques, 123 Avenue, Albert Thomas, F-87060 Limoges, France.
Teste
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K
Zerrouki
R
R
Champavier
Y
Y
Guilloton
M
M
D000478:Alkylation; D002614:Chelating Agents / Q000737:chemistry*; D043844:Crown Ethers / Q000737:chemistry; D003841:Deoxycytidine / Q000737:chemistry; D003857:Deoxyuridine / Q000737:chemistry; D017097:Electric Impedance; D011741:Pyrimidine Nucleosides / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013936:Thymidine / Q000737:chemistry
D002614:Chelating Agents; D043844:Crown Ethers; D011741:Pyrimidine Nucleosides; D012997:Solvents; D003841:Deoxycytidine; D013936:Thymidine; D003857:Deoxyuridine