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Synthesis and Structure Assignment of 1-[(2-Hydroxyethoxy)methyl]- and 1-[(1,3-Dihydroxy-2-propoxy)methyl]-6-azaisocytosine
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1995
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Bioorganic ChemistryLh-13c Heteronuclear CorrelationBiochemistryHeterocyclicNatural SciencesGlycobiologyMolecular BiologyOrganic ChemistryStructure AssignmentStereoselective SynthesisChemistryHeterocycle ChemistryM ExperimentsNatural Product SynthesisSynthetic ChemistryUnambiguous AssignmentGlycosylation
Abstracl-1-[(2-Acetoxyethoxy)methyll-6-azaisocytone and 1-[(1,3dibenzyloxy-2-propoxy)methyl]-6-azaisocytosine have been prepared, and their unambiguous assignment of 1H and 13C peaks through the LH-13C heteronuclear correlation (HETCOR) n m experiments is described.The X-ray crystallographic amalysis reveals unambiguously the site of glycosylation at N1. Deprotection of both acyclonucleosides provided 1-[(2-hydroxyethoxy)methyl]-6-azaisocytosine and 1-[(1.3-dihy~oxy-2-propoxy)methy1]-6-azaisocytosine,respectively.