5-O-methyl 1-O-phenyl (3S)-3-hydroxy-3,6-dihydro-2H-pyridine-1,5-dicarboxylate | 323201-33-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 5-O-methyl 1-O-phenyl (3S)-3-hydroxy-3,6-dihydro-2H-pyridine-1,5-dicarboxylate
• CAS: 323201-33-8
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: RXWIJHFVUMXFAY-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-methyl 1-O-phenyl (3S)-3-hydroxy-3,6-dihydro-2H-pyridine-1,5-dicarboxylate 在 铂 盐酸 、 lithium hydroxide 、 硼烷 、 双氧水 、 氧气 、 sodium acetate 作用下， 以 四氢呋喃 为溶剂， 生成 (3R,4R,5S)-5-carboxypiperidine-3,4-diol
  参考文献：
  名称：

  Selective Fowler Reductions:  Asymmetric Total Syntheses of Isofagomine and Other 1-Azasugars from Methyl Nicotinate

  摘要：

  [GRAPHICS]An efficient, high-yielding strategy has been developed for the asymmetric synthesis of 1-N-iminosugars (1-azasugars), a new class of glycosidase inhibitors with promising biomedical applications. A highly regioselective procedure for the 1,2-reduction of substituted pyridines was employed to transform methyl nicotinate into several representative 1-azasugars.

  DOI：

  10.1021/ol006810x
• 作为产物：
  描述：

  烟酸甲酯 在 2-乙胺吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 jones reagent 、 三氟甲磺酸三甲基硅酯 、 N-甲基麻黄碱 、 硼烷 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 18.0h， 生成 5-O-methyl 1-O-phenyl (3S)-3-hydroxy-3,6-dihydro-2H-pyridine-1,5-dicarboxylate
  参考文献：
  名称：

  Selective Fowler Reductions:  Asymmetric Total Syntheses of Isofagomine and Other 1-Azasugars from Methyl Nicotinate

  摘要：

  [GRAPHICS]An efficient, high-yielding strategy has been developed for the asymmetric synthesis of 1-N-iminosugars (1-azasugars), a new class of glycosidase inhibitors with promising biomedical applications. A highly regioselective procedure for the 1,2-reduction of substituted pyridines was employed to transform methyl nicotinate into several representative 1-azasugars.

  DOI：

  10.1021/ol006810x

文献信息

• Selective Fowler Reductions:  Asymmetric Total Syntheses of Isofagomine and Other 1-Azasugars from Methyl Nicotinate
  作者：Guohua Zhao、Urmila C. Deo、Bruce Ganem

  DOI：10.1021/ol006810x

  日期：2001.1.1

  [GRAPHICS]An efficient, high-yielding strategy has been developed for the asymmetric synthesis of 1-N-iminosugars (1-azasugars), a new class of glycosidase inhibitors with promising biomedical applications. A highly regioselective procedure for the 1,2-reduction of substituted pyridines was employed to transform methyl nicotinate into several representative 1-azasugars.