Synthesis of 3-Acetamido-3-deoxy-(1→5)-α-D-ribofuranan by Ring-Opening Polymerization of 1,4-Anhydro-3-azido-α-D-ribopyranose Derivative

DOI Web Site 被引用文献1件 参考文献47件 オープンアクセス

書誌事項

タイトル別名
  • Synthesis of 3-Acetamido-3-deoxy-(1.RAR.5)-.ALPHA.-D-ribofuranan by Ring-Opening Polymerization of 1,4-anhydro-3-azido-.ALPHA.-D-ribopyranose Derivative.
  • Synthesis of 3 Acetamido 3 deoxy 1 5 アルファ D ribofuranan by Ring-Opening
公開日
1999
DOI
  • 10.1295/polymj.31.167
公開者
The Society of Polymer Science, Japan

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説明

A stereoregular 3-acetamido-3-deoxy-(1→5)-α-D-ribofuranan (3AAdRF) was synthesized by the synthetic route starting from selective ring-opening polymerization of 1,4-anhydro-3-azido-2-O-t-butyldimethylsilyl-3-deoxy-α-D-ribopyranose (A3ASR). A3ASR was polymerized by BF3·OEt2 catalyst at low temperature to give 3-azido-2-O-t-butyl-dimethylsilyl-(1→5)-α-D-ribofuranan (3AzSRF) with \\barMn of 1.4×104—1.9×104 and [α]D of +249—+266°. 3AzSRF was reduced with NaBH4 in a tetrahydrofuran (THF)–ethanol mixture to afford 3-amino-2-O-t-butyldimethylsilyl-3-deoxy-(1→5)-α-D-ribofuranan (3AmSRF). Acetylation of the amino group in 3AmSRF produced 3-acetamido-ribofuranan derivative (3AAdSRF), and then desilylation of the 3AAdSRF gave 3AAdRF with \\barMn ranging from 9.4×103 to 10.5×103 and [α]d of +195°. The structure analysis was performed by 13C and 1H NMR spectroscopy, IR spectroscopy, and optical rotation measurements.

収録刊行物

  • Polymer Journal

    Polymer Journal 31 (2), 167-171, 1999

    The Society of Polymer Science, Japan

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