2,3,4-tri-O-benzoyl-6-O-chloroacetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate | 1063698-04-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate
• CAS: 1063698-04-3
• 化学式: C₅₈H₄₇Cl₄NO₁₈
• 分子量: 1187.82
• InChiKey: UYMJMNDVBFFQCZ-JUHRREKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.95
• 重原子数：
  81.0
• 可旋转键数：
  19.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  244.87
• 氢给体数：
  1.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-6-O-chloroacetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate 、 (2S,3R,4E)-3-O-benzoyl-2-hexadecanamido-4-octadecene-1,3-diol 在 三氟甲磺酸三甲基硅酯 、 4 Angstroem MS 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以62%的产率得到2,3,4-tri-O-benzoyl-6-O-chloroacetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranosyl-(1->1)-(2S,3R,4E)-3-O-benzoyl-2-hexadecanamido-4-octadecene-1,3-diol
  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：

  、 三氯乙腈 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate
  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