Michael addition reactions of some nucleobases to 1-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitro-beta-D- hexopyran osyl) uracil.
Michael addition of cytosine, N4-dimethyl-aminomethylidene-cytosine, uracil and thymine to the nitroolefin (2) generated in situ from 1-(4,6-O-benzylidene-3-deoxy-3-nitro-beta-D-glucopyranosyl)-uracil (1) gave the corresponding 2-(N1-pyrimidinyl)-2,3-dideoxy-3-nitro-beta-D-glucopyranosides (3-6). Compound 3 was also obtainable from 4.
Hibino
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H
Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Japan.
Minamoto
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K
Suzuki
S
S
Ukai
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T
D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D003596:Cytosine / Q000031:analogs & derivatives / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013941:Thymine / Q000737:chemistry*; D014498:Uracil / Q000737:chemistry*; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
C113081:1-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitrohexopyranosyl)uracil; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007202:Indicators and Reagents; D009705:Nucleosides; D014498:Uracil; D003596:Cytosine; D013941:Thymine; D014529:Uridine