Studies on Nucleosides and Nucleotides. XI. Nucleophilic Substitution of Secondary Sulfonyloxy Groups of Pyrimidine Nucleosides. IV. Deamination in Isocytosine Derivatives and Dealkoxylation in 2-O-Alkyl-pyrimidine Nucleosides

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概要

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• 1-(2', 3'-Epoxy-β-D-lyxofuranosyl) isocytosines (I) and (II) were easily deaminated by heating with aqueous hydrogen chloride, yielding 2,2'-anhydro-1-(3'-chloro-3'-deoxy-β-D-arabinofuranosyl) uracil (III), and 1-(3'-chloro-3'-deoxy-β-D-arabinofuranosyl) uracil (IV). And other isocytosine derivatives (VIII), (X), (XI), and (XVI) were also deaminated by heating at 80° for several minutes in acetic acid to corresponding anhydronucleosides, i.e. VII, IX, and XV, while 2', 3'-O-isopropylideneisocytidine (XVII) and isocytidine (XVIII) were not deaminated. Furthermore, demethoxylation of 2-O-methylpyrimidine nucleosides was studied. In the reaction of 2,5'-anhydro-1-(2,3'-di-O-acetyl-β-D-arabinofuranosyl) uracil (XXI) with triethylamine in methanol, 2-O-methyl-1-β-D-arabinofuranosyluracil (XXII) was not obtained, but IX as a sole product. This phenomenon showed that XXII was the intermediate. However, 2-O-methyl-1-(2', 3'-epoxy-β-D-lyxofuranosyl) uracil (XXIII), 2-O-methyl-1-(2', 3'-O-isopropylidene-β-D-ribofuranosyl) uracil (XXIV) and 2-O-methyluridine (XXV) were not demethoxylated by heating at 80° in acetic acid. Therefore, deamination in isocytosine derivatives and demethoxylation in 2-O-methylpyrimidine derivatives required one hydroxy group of up form in 2'-position or 2', 3'-epoxide ring of lyxo-form.

• 公益社団法人日本薬学会の論文
• 1968-03-25

著者

• 平田 三四司

  Central Research Laboratory Daiichi Seiyaku Co. Ltd.

関連論文

• Studies on Nucleosides and Nucleotides. VIII. Nucleophilic Substitution of Secondary Sulfonyloxy Groups of Pyrimidine Nucleosides. (1)
• The Nucleophilic Substitution of Secondary Sulfonyloxy Groups of Pyrimidine Nucleosides
• Studies on Nucleosides and Nucleotides. XII. Syntheses of 3'-Amino-3'-deoxypentofuranosylcytosines
• Studies on Nucleosides and Nucleotides. XI. Nucleophilic Substitution of Secondary Sulfonyloxy Groups of Pyrimidine Nucleosides. IV. Deamination in Isocytosine Derivatives and Dealkoxylation in 2-O-Alkyl-pyrimidine Nucleosides
• Studies on Nucleosides and Nucleotides. X. Nucleophilic Substitution of Secondary Sulfonyloxy Groups of Pyrimidine Nucleosides. III. Reaction of 2', 3'-Di-O-tosyluridine with Methanolic Ammonia
• Studies on Nucleosides and Nucleotides. IX. Nucleophilic Substitution of Secondary Sulfonyloxy Groups of Pyrimidine Nucleosides. II. Reaction of 2,2'-Anhydro-1-(3'-O-tosyl-β-D-arabinofuranosyl) uracil with Sodium Bromide, Sodium Ethanethiol, and Sodium Az
• Studies on Nucleosides and Nucleotides. I. Synthesis of Glycosylthymines from Glycosylureas.

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