2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)]-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate | 1394170-36-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)]-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate
• CAS: 1394170-36-5
• 化学式: C₄₁H₅₀Cl₃NO₂₂
• 分子量: 1015.2
• InChiKey: GTGMCJPMQLHQCL-MZVWROGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  67.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  281.79
• 氢给体数：
  1.0
• 氢受体数：
  23.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)]-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate 、 偏诺皂苷元 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到pennogenin 3-O-[2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)]-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)]-4,6-O-benzylidene-β-D-glucopyranoside
  参考文献：
  名称：

  The synthesis of pennogenin 3-O-β-d-glucopyranosyl-(1 → 3)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside

  摘要：

  Pennogenin 3-O-beta-D-glucopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-beta-D-glucopyranoside, a monodesmosidic saponin isolated from Paris polyphylla Smith var. yunnanensis with promised antitumor activities, was firstly synthesized from glucoside thiol via nine steps and with 27% overall yield.

  DOI：

  10.1080/10286020.2011.653348
• 作为产物：
  描述：

  phenyl 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 三氟化硼乙醚 、 水 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 3.5h， 生成 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1->2)-[(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)]-4,6-O-benzylidene-α-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  The synthesis of pennogenin 3-O-β-d-glucopyranosyl-(1 → 3)-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside

  摘要：

  Pennogenin 3-O-beta-D-glucopyranosyl-(1 -> 3)-[alpha-L-rhamnopyranosyl-(1 -> 2)]-beta-D-glucopyranoside, a monodesmosidic saponin isolated from Paris polyphylla Smith var. yunnanensis with promised antitumor activities, was firstly synthesized from glucoside thiol via nine steps and with 27% overall yield.

  DOI：

  10.1080/10286020.2011.653348