Synthesis of Dinucleoside (N3‘→MeP5‘) Methanephosphonamidates

Three different approaches were used for the synthesis of dinucleoside methanephosphonamidates [3‘-NH-P(O)(CH3)O-5‘], starting from dichloromethylphosphine or dichloromethanephosphonate as the phosphorus-containing moiety. 5‘-DMT-3‘-amino-3‘-deoxythymidine and N(4)-benzoyl-5‘-DMT-3‘-amino-2‘,3‘-dide...

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Bibliographic Details
Published in:Organic letters 2002-05, Vol.4 (10), p.1799-1802
Main Authors: Nawrot, Barbara, Sobczak, Milena, Antoszczyk, Slawomir
Format: Article
Language:English
Subjects:
Chromatography, High Pressure Liquid
Chromatography, Thin Layer
Circular Dichroism
Dinucleoside Phosphates - chemical synthesis
Dinucleoside Phosphates - chemistry
DNA - chemistry
DNA - drug effects
Magnetic Resonance Spectroscopy
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - chemistry
Spectrometry, Mass, Fast Atom Bombardment
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Summary:Three different approaches were used for the synthesis of dinucleoside methanephosphonamidates [3‘-NH-P(O)(CH3)O-5‘], starting from dichloromethylphosphine or dichloromethanephosphonate as the phosphorus-containing moiety. 5‘-DMT-3‘-amino-3‘-deoxythymidine and N(4)-benzoyl-5‘-DMT-3‘-amino-2‘,3‘-dideoxycytidine were used as the aminonucleoside precursors and the respective 3‘-protected nucleosides (thymidine or N(4)-benzoyl-2‘-deoxycytidine) as the 5‘-hydroxyl reagents.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0259084