Synthetic Nucleosides and Nucleotides. VI. On the Several Routes for the Syntheses of 4-Thiouridylic Acid Homologues

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概要

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• The following synthetic methods for the preparation of 4-thiouridylic acid homologues from uridine are described. Route A. Mild acid treatment of 2', 3'-O-isopropylidene-5'-O-benzoyl-4-thiouridine (II) followed by phosphorylation by Tener's procedure gave 4-thiouridine 2', (3')-phosphate via 5'-O-benzoyl-4-thiouridine (III). Alkali treatment of II followed by phosphorylation by Tener's procedure gave 4-thiouridine 5'-phosphate via 2', 3'-O-isopropylidene-4-thiouridine (IV). Route B. 2', 3'-Di-O-acetyl-5'-O-trityl-4-thiouridine (V) was prepared by thiation of 2,3'-di-O-acetyl-5'-O-trityluridine. Alkali treatment of V followed by Tener's phosphorylation gave 2', (3')-phosphate of 4-thiouridine via 5'-O-trityl-4-thiouridine (VI). Mild acid treatment of V followed by Tener's phosphorylation gave 5'-phosphate of 4-thiouridine in satisfactory yield via 2', 3'-di-O-acetyl-4-thiouridine (VII). Route C. Direct phosphorylation of 4-thiouridine with excess amounts of cyanoethylphosphate and dicyclohexylcarbodiimide produced 2', (3')-mono-, 5'-mono-and 2', (3'), 5'-diphosphate of 4-thiouridine. Treatment of the diphosphate with dicyclohexylcarbodiimide gave 4-thiouridine 2', 3'-cyclic, 5'-diphosphate (VIII). 4-Thiouridine 2', 3'-cyclic phosphate (IX) was obtained by treatment of 4-thiouridine 2', (3')-phosphate with same manner or by digestion of VIII with E. coli alkaline phosphomonoesterase. 4-thiouridine 3'-phosphate was prepared by digestion of IX with bovine pancreatic ribonuclease.

• 公益社団法人日本薬学会の論文
• 1969-01-25

著者

• 実吉 峯郎

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 実吉 峯郎

  National Cancer Center Research Institute

• 沢田 文夫

  Chemistry Divison National Institute Of Radiological Sciences

関連論文

• Synthetic Nucleosides and Nucleotides. XVI. Synthesis and Biological Evaluations of a Series of 1-β-D-Arabinofuranosylcytosine 5'-Alkyl or Arylphosphates
• Mode of Action of 5-Fluorocytidine and 5-Fluoro-2'-deoxycytidine in L5178Y Cells in Vitro
• Synthetic Nucleosides and Nucleotides. XIII. Stannic Chloride Catalyzed Ribosylation of Several 6-Substituted Purines
• Synthetic Nucleosides and Nucleotides. I. On Synthesis and Properties of Several Thiocyanato Derivatives of Purines and Their Ribonucleosides.
• Biological Photochemistry. I. The Correlation between the Photodynamical Behaviors and the Chemical Structures of Nucleic Acid-bases, Nucleosides, and Related Compounds in the Presence of Methylene-blue
• Resistance of Cyclocytidine to Cytidine Deaminase
• Synthetic Nucleosides and Nucleotides. XVIII. Synthesis and Cytostatic Activity of 5-Fluoropyrimidine Nucleosides of 3-Amino-3-deoxy-β-D-ribofuranose and Related Compounds
• Synthetic Nucleosides and Nucleotides. XIX. Synthesis of 3'-Deoxycytidine 5'-Triphosphate and Related 3'-Deoxy-ribonucleotides from Cordycepin'
• Studies on Hydrogen Exchange. XII. Reaction Mechanism for Hydrogen Exchange of C-8 Hydrogen of Purine Ribosides
• The Correlation between the Antitumor Activities and Chemical Structures of Thiocyanato Derivatives of Purines and Their Ribonucleosides
• Synthetic Nucleosides and Nucleotides. XXVII. Selective Inhibition of Deoxyribonucleic Acid Polymerase α by 1-β-D-Arabinofuranosyl-5-styryluracil 5'-Triphosphates and Related Nucleotides : Influence of Hydrophobic and Steric Factors on the Inhibitory Acti
• Synthetic Nucleosides and Nucleotides. XI. : Facile Synthesis and Antitumor Activities of Various 5-Fluoropyrimidine Nucleosides
• Synthetic Nucleosides and Nucleotides. XXVIII. : Synthesis of 5-Alkylcytidines from 5-Alkylbarbituric Acids
• Synthetic Nucleosides and Nucleotides. XV. 5-Dimethylamino-2-oxidoisoquinolin-1-yl Diazomethane : A Novel Water-soluble Fluorescent Labelling Agent for Nucleotides
• Synthetic Nucleosides and Nucleotides. IX. Synthesis of 2', 5'- and 3', 5'-Di-O-tritylcytidine and the Related Compounds via Thiation
• Synthetic Nucleosides and Nucleotides. VIII. Direct Synthesis of the 5'-Phosphate of 4-Thiouridine, 6-Thioinosine and 6-Thioguanosine from the Corresponding Oxy Nucleotide via Thiation Procedure
• Synthetic Nucleotides. VII. A Direct Replacement of 6-Thiol Group of 6-Thioinosine with Hydrazine Hydrate
• Synthetic Nucleosides and Nucleotides. VI. On the Several Routes for the Syntheses of 4-Thiouridylic Acid Homologues
• Synthesis and Reaction of 3-Fluoro-4-nitroquinoline 1-Oxide
• Synthetic Nucleosides and Nucleotides. III. On the Syntheses of Several 2,6,8-Trisubstituted Purine Ribonucleosides
• Direct Thiation of Uridine 5'-Phosphate
• Syntheses and Properties of Several 4-Alkyl-or Arylsulfonylquinoline 1-Oxides

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