Synthesis of the Optically Active Carbocyclic Analogs of the Four 2′-Deoxyribonucleoside Monophosphates

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• Abbreviations used: C-dAMP, β-D-Carbocyclic-1′-(9H-adenin-9-yl)-2′- deoxyribonucleoside 5′-monophosphate, or (1S, 2R, 4R)-4-(9H-adenin-9-yl)- 2-[(phosphoryloxy)methyl]-cyclopentan-1-ol; C-dGMP, β-D-Carbocyclic-1′-(9H-guanin-9-yl)-2′-deoxyribonucleoside 5′-monophosphate, or (1S, 2R, 4R)-4-(9H-guanin-9-yl)-2-[(phosphoryloxy)methyl]-cyclopentan-1-ol; C-dCMP, β-D-Carbocyclic-1′-(1H-cytosin-1-yl)-2′-deoxyribonucleoside 5′-monophosphate or (1S, 2R, 4R)-4-(1H-cytosin-1-yl)-2-[(phosphoryloxy)-methyl]-cyclopentan-1-ol; C-dTMP, β-D-Carbocyclic-1′-(1H-thymin-1-yl)-2′-deoxyribonucleoside 5′-monophosphate or (1S, 2R, 4R)-2-(phosphoryloxymethyl)-4-(1H-thymin-1-yl) cyclopentan-1-ol; BOM, benzyloxymethyl; DEAD, diethyl azodicarboxylate; DMAP, 4-dimethylaminopyridine; DMF, N,N-dimethylformamide; DMSO, dimethyl sulfoxide; mCPBA, meta-chloroperbenzoic acid; TBAF, tetrabutylammonium fluoride; THF, tetrahydrofuran; TLC, thin layer chromatography; TMS, tetramethylsilane
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