2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside | 1063698-13-4

• 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-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
• CAS: 1063698-13-4
• 化学式: C₅₉H₅₈O₁₇Si
• 分子量: 1067.18
• InChiKey: XMHWVMKYBCWRSV-YCLOOVGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.15
• 重原子数：
  77.0
• 可旋转键数：
  20.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  214.95
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-β-D-galactopyranoside 、 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 、 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以60%的产率得到2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi

  摘要：

  Two types of amphoteric glycosphingolipid found in the earthworm Pheretima hilgendorfi, PC(-> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 1)Cer (1) and PC(-> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 1)Cer (2), and their derivatives (4, 5) were synthesized. These were examined for their ability to enhance production of interleukin-8 (IL-8), a potent inflammatory cytokine involved in neutrophil chemotaxis, in a TNF alpha-stimulated granulocytic HL-60 cells. Compounds 1 and 2 were found to be potent enhancers of IL-8 production. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.05.001
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 吡啶 、 硫脲 作用下， 以 乙醇 为溶剂， 反应 2.5h， 以88%的产率得到2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthetic studies on glycosphingolipids from Protostomia phyla: syntheses and biological activities of amphoteric glycolipids containing a phosphocholine residue from the earthworm Pheretima hilgendorfi

  摘要：

  Two types of amphoteric glycosphingolipid found in the earthworm Pheretima hilgendorfi, PC(-> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 1)Cer (1) and PC(-> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 6)-beta-D-Galp-(1 -> 1)Cer (2), and their derivatives (4, 5) were synthesized. These were examined for their ability to enhance production of interleukin-8 (IL-8), a potent inflammatory cytokine involved in neutrophil chemotaxis, in a TNF alpha-stimulated granulocytic HL-60 cells. Compounds 1 and 2 were found to be potent enhancers of IL-8 production. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.05.001