Transnucleosidation : An Improved Method for Transglycosylation from Pyrimidines to Purines

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概要

• 論文の詳細を見る

• Transglycosylation from acylated pyrimidine nucleoside to purines was originally developed by Miyaki, et al. To apply this method to the naturally occurring pyrimidine nucleosides having a labile sugar moiety, we studied the improvement of this reaction. As model compounds, tri-O-acetyl-3-benzoyluridine (1) and tetraacetylcytidine (2) were employed. Reaction conditions and yields were greatly improved by utilizing (1) trimethylsilyl derivatives of exo-N-acylpurines as a glycosyl acceptor, (2) trimethylsilyl trifluoromethanesulfonate as a catalyst in acetonitrile-dichloroethane. Because of the mild reaction conditions and high yield, this procedure may be regarded as a versatile method for transglycosylation, which was shown by the successful preparation of purine analogs of the polyoxin and octosyl acid nucleosides having labile amino-or anhydrosugar uronic acid.

• 公益社団法人日本薬学会の論文
• 1977-12-25

著者

• 磯野 清

  The Institute Of Physical And Chemical Research

• 東 常政

  The Institute of Physical and Chemical Research

• 東 常政

  The Institute Of Physical And Chemical Research:(present Address)research Division Kaken Chemical Co

関連論文

• Studies on the Biological Activities of Islandic Acid and Related Compounds
• Transnucleosidation : An Improved Method for Transglycosylation from Pyrimidines to Purines
• Polyoxin Analogs. III. Synthesis and Biological Activity of Aminoacyl Derivatives of Polyoxins C and L
• Formation and Characterization of 5'-Deoxy-5', 6-epimino-5,6-dihydro-2', 3'-O-isopropylideneuridine
• Polyoxin Analogs. I. Synthesis of Aminoacyl Derivatives of 5'-Amino-5'-deoxyuridine

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