(2S,3R)-1-(3''-deoxy-3''-fluoro-α-D-galactopyranosyl)-2-hexacosanoyloaminooctadecane-3-ol | 1186196-01-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-1-(3''-deoxy-3''-fluoro-α-D-galactopyranosyl)-2-hexacosanoyloaminooctadecane-3-ol
• 英文别名: N-[(2S,3R)-1-[(2S,3S,4S,5S,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxyoctadecan-2-yl]hexacosanamide
• CAS: 1186196-01-9
• 化学式: C₅₀H₉₈FNO₇
• 分子量: 844.329
• InChiKey: VVDZCDNBNOMKDJ-LXQBDVMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.2
• 重原子数：
  59
• 可旋转键数：
  44
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2S,3R)-3-benzyloxy-1-(3''-deoxy-3''-fluoro-2'',4'',6''-tri-O-benzyl-α-D-galactopyranosyl)-2-(N-hexacosanoyloamino)octadecane 在 20% palladium hydroxide on carbon 、 氢气 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 24.0h， 以71%的产率得到(2S,3R)-1-(3''-deoxy-3''-fluoro-α-D-galactopyranosyl)-2-hexacosanoyloaminooctadecane-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

文献信息

• Synthesis and evaluation of 3″- and 4″-deoxy and -fluoro analogs of the immunostimulatory glycolipid, KRN7000
  作者：Ravinder Raju、Bernard F. Castillo、Stewart K. Richardson、Meena Thakur、Ryan Severins、Mitchell Kronenberg、Amy R. Howell

  DOI：10.1016/j.bmcl.2009.06.005

  日期：2009.8

  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.