dimethyl (3S,4S,5R)-4-benzyloxy-3,5-dihydroxy-1-cyclohexenephosphonate | 877760-76-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl (3S,4S,5R)-4-benzyloxy-3,5-dihydroxy-1-cyclohexenephosphonate
• CAS: 877760-76-4
• 化学式: C₁₅H₂₁O₆P
• 分子量: 328.302
• InChiKey: LMHIBFCESIUUGN-RRFJBIMHSA-N

物化性质

• 沸点：
  494.5±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dimethyl (3S,4S,5R)-4-benzyloxy-3,5-dihydroxy-1-cyclohexenephosphonate 在 palladium on activated charcoal 吡啶 、 ammonium hydroxide 、 偶氮二甲酸二异丙酯 、 1,3-环己二烯 、 苯硫酚 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 166.0h， 生成 ammonium [α-D-galactopyranos-6-yl (3S,4S,5R)-3,4,5-trihydroxy-1-cyclohexenephosphonate]
  参考文献：
  名称：

  Building a successful structural motif into sialylmimetics—cyclohexenephosphonate monoesters as pseudo-sialosides with promising inhibitory properties

  摘要：

  A variable synthesis of a new class of sialylmimetics which provides access to pseudo-sialosides containing the successful cyclohexene motif in the sialic acid mimicking part has been developed. The D- and L-xylo cyclohexenephosphonate scaffolds allow attachment of selected aglycons or aglycon mimetics via mixed phosphonate diester strategies and some target compounds thus synthesized displayed promising inhibitory properties when tested with parasitic or bacterial sialidases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.025
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以45%的产率得到dimethyl (3S,4S,5R)-4-benzyloxy-3,5-dihydroxy-1-cyclohexenephosphonate
  参考文献：
  名称：

  Building a successful structural motif into sialylmimetics—cyclohexenephosphonate monoesters as pseudo-sialosides with promising inhibitory properties

  摘要：

  A variable synthesis of a new class of sialylmimetics which provides access to pseudo-sialosides containing the successful cyclohexene motif in the sialic acid mimicking part has been developed. The D- and L-xylo cyclohexenephosphonate scaffolds allow attachment of selected aglycons or aglycon mimetics via mixed phosphonate diester strategies and some target compounds thus synthesized displayed promising inhibitory properties when tested with parasitic or bacterial sialidases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.025