methyl 1-bromo-2,4-di-O-acetyl-3-O-pivaloyl-α-L-idopyranuronate | 1062272-95-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 1-bromo-2,4-di-O-acetyl-3-O-pivaloyl-α-L-idopyranuronate
• CAS: 1062272-95-0
• 化学式: C₁₆H₂₃BrO₉
• 分子量: 439.257
• InChiKey: WOCWOCBSZASXDP-KIJLLGNVSA-N

物化性质

• 沸点：
  420.0±45.0 °C(predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

反应信息

• 作为反应物：
  描述：

  methyl 1-bromo-2,4-di-O-acetyl-3-O-pivaloyl-α-L-idopyranuronate 在 三乙胺 、 tetrabutylammonium phosphate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 生成 methyl 1-phospho-2,4-di-O-acetyl-3-O-pivaloyl-β-L-idopyranuronate
  参考文献：
  名称：

  Synthesis of Uridine 5′-diphosphoiduronic Acid: A Potential Substrate for the Chemoenzymatic Synthesis of Heparin

  摘要：

  An improved understanding of the biological activities of heparin requires structurally defined heparin oligosaccharides. The chemoenzymatic synthesis of heparin oligosaccharides relies on glycosyltransferases that use UDP-sugar nucleotides as donors. Uridine 5'-diphosphoiduronic acid (UDP-IdoA) and uridine 5'-diphosphohexenuronic acid (UDP-HexUA) have been synthesized as potential analogues of uridine 5'-diphosphoglucuronic acid (UDP-GlcA) for enzymatic incorporation into heparin oligosaccharides. Non-natural UDP-IdoA and UDP-HexUA were tested as substrates for various glucuronosyltransferases to better understand enzyme specificity.

  DOI：

  10.1021/jo801409c
• 作为产物：
  描述：

  methyl 1,2,4-tri-O-acetyl-3-O-pivaloyl-β-L-idopyranuronate 在 三溴化磷 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 3.17h， 生成 methyl 1-bromo-2,4-di-O-acetyl-3-O-pivaloyl-α-L-idopyranuronate
  参考文献：
  名称：

  Synthesis of Uridine 5′-diphosphoiduronic Acid: A Potential Substrate for the Chemoenzymatic Synthesis of Heparin

  摘要：

  An improved understanding of the biological activities of heparin requires structurally defined heparin oligosaccharides. The chemoenzymatic synthesis of heparin oligosaccharides relies on glycosyltransferases that use UDP-sugar nucleotides as donors. Uridine 5'-diphosphoiduronic acid (UDP-IdoA) and uridine 5'-diphosphohexenuronic acid (UDP-HexUA) have been synthesized as potential analogues of uridine 5'-diphosphoglucuronic acid (UDP-GlcA) for enzymatic incorporation into heparin oligosaccharides. Non-natural UDP-IdoA and UDP-HexUA were tested as substrates for various glucuronosyltransferases to better understand enzyme specificity.

  DOI：

  10.1021/jo801409c