(2S,3R)-1-(2'',3'',6''-tri-O-benzyl-4''-deoxy-4''-fluoro-α-D-galactopyranosyl)-3-benzyloxy-2-(N-hexacosanoylamino)ictadecane | 1186196-23-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: (2S,3R)-1-(2'',3'',6''-tri-O-benzyl-4''-deoxy-4''-fluoro-α-D-galactopyranosyl)-3-benzyloxy-2-(N-hexacosanoylamino)ictadecane
• CAS: 1186196-23-5
• 化学式: C₇₈H₁₂₂FNO₇
• 分子量: 1204.83
• InChiKey: WUSSUUBYUFUTIT-JLVXIOOISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21.39
• 重原子数：
  87.0
• 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)-1-(2'',3'',6''-tri-O-benzyl-4''-deoxy-4''-fluoro-α-D-galactopyranosyl)-3-benzyloxy-2-(N-hexacosanoylamino)ictadecane 在 氢气 、 palladium(II) hydroxide 作用下， 以 乙醇 、 氯仿 为溶剂， 以69%的产率得到(2S,3R)-1-(4''-deoxy-4''-fluoro-α-D-galactopyranosyl)-2-hexacosanoylaminooctadecan-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 、 phenyl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 以21%的产率得到(2S,3R)-1-(2'',3'',6''-tri-O-benzyl-4''-deoxy-4''-fluoro-α-D-galactopyranosyl)-3-benzyloxy-2-(N-hexacosanoylamino)ictadecane
  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