(2S,3R)-3-benzyloxy-1-(2'',4'',6''-tri-O-benzyl-3''-deoxy-α-D-galactopyranosyl)-2-hexacosanoylaminooctadecane | 1186196-14-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2S,3R)-3-benzyloxy-1-(2'',4'',6''-tri-O-benzyl-3''-deoxy-α-D-galactopyranosyl)-2-hexacosanoylaminooctadecane
• CAS: 1186196-14-4
• 化学式: C₇₈H₁₂₃NO₇
• 分子量: 1186.84
• InChiKey: AIJQRLYSANCNEK-DELYITEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.44
• 重原子数：
  86.0
• 可旋转键数：
  56.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  84.48
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,3R)-3-benzyloxy-1-(2'',4'',6''-tri-O-benzyl-3''-deoxy-α-D-galactopyranosyl)-2-hexacosanoylaminooctadecane 在 20% palladium hydroxide on carbon 、 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 28.0h， 以46%的产率得到(2S,3R)-1-(3''-deoxy-α-D-galactopyranosyl)-2-hexacosanoylaminooctadecane-3-ol
  参考文献：
  名称：

  Synthesis and evaluation of 3″- and 4″-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000

  摘要：

  Four 3 ''- and 4 ''-deoxy and -fluorogalactosyl ceramides were synthesized, and their ability to stimulate iNKT cells, based on levels of IL-2 production, was assessed in three NKT cell receptor hybridomas. In two of the hybridomas, 1.2 and 2H4, all of the analogs were immunostimulatory, while in the 1.4 hybridoma only the 4 ''-fluoro analog led to the production of significant levels of IL-2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.005
• 作为产物：
  描述：

  (2S,3R)-3-O-benzyl-2-(N-hexacosanoylamino)octadecan-1,3-diol 、 2-pyridyl 2,4,6-tri-O-benzyl-3-deoxy-1-thio-β-D-xylo-hexapyranose 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以10%的产率得到(2S,3R)-3-benzyloxy-1-(2'',4'',6''-tri-O-benzyl-3''-deoxy-α-D-galactopyranosyl)-2-hexacosanoylaminooctadecane
  参考文献：
  名称：

  Synthesis and evaluation of 3″- and 4″-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000

  摘要：

  Four 3 ''- and 4 ''-deoxy and -fluorogalactosyl ceramides were synthesized, and their ability to stimulate iNKT cells, based on levels of IL-2 production, was assessed in three NKT cell receptor hybridomas. In two of the hybridomas, 1.2 and 2H4, all of the analogs were immunostimulatory, while in the 1.4 hybridoma only the 4 ''-fluoro analog led to the production of significant levels of IL-2. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.005