(2S,3S,4R)-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-2-tetracosanoylamino-1,3,4-nonanetriol | 1375103-10-8

• 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,3S,4R)-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-2-tetracosanoylamino-1,3,4-nonanetriol
• CAS: 1375103-10-8
• 化学式: C₆₉H₁₀₃NO₁₀
• 分子量: 1106.58
• InChiKey: WIQJAPHBALYPGI-YDYWTUKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.73
• 重原子数：
  80.0
• 可旋转键数：
  44.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  112.17
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2S,3S,4R)-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-2-tetracosanoylamino-1,3,4-nonanetriol 在 盐酸 、 20 % Pd(OH)2/C 、 氢气 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 5.5h， 生成 (2S,3S,4R)-1-O-(α-D-galactosyl)-6-oxa-2-tetracosanoylamino-1,3,4-nonanetriol
  参考文献：
  名称：

  Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile

  摘要：

  A series of truncated analogs of alpha-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-gamma ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.025
• 作为产物：
  描述：

  (2R,3R,4R)-1,3,4-trihydroxy-5-propoxypentan-2-yl methanesulfonate 在 sodium azide 、 四丁基溴化铵 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 90.75h， 生成 (2S,3S,4R)-3,4-O-isopropyliden-6-oxa-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactosyl)-2-tetracosanoylamino-1,3,4-nonanetriol
  参考文献：
  名称：

  Synthesis and biological evaluation of truncated α-galactosylceramide derivatives focusing on cytokine induction profile

  摘要：

  A series of truncated analogs of alpha-galactosylceramide with altered ceramide moiety was prepared, and evaluated for Th2-biased response in the context of IL-4/IFN-gamma ratio. Phytosphingosine-modified analogs including cyclic, aromatic and ethereal compounds as well as the C-glycoside analog of OCH (2) with their cytokine inducing profile are disclosed. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.025