Acetic acid (2S,3R)-2-tetradecanoylamino-3-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-octadecyl ester | 222055-61-0

• 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: Acetic acid (2S,3R)-2-tetradecanoylamino-3-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-octadecyl ester
• 英文别名: [(2S,3R)-2-(tetradecanoylamino)-3-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoctadecyl] acetate
• CAS: 222055-61-0
• 化学式: C₆₈H₁₀₁NO₉
• 分子量: 1076.55
• InChiKey: RQLZMHJFQBXQOV-HUSLVVDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.8
• 重原子数：
  78
• 可旋转键数：
  46
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R)-2-tetradecanoylamino-3-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-octadecyl ester 在 钯 甲醇 、 氢气 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 Tetradecanoic acid [(1S,2R)-1-hydroxymethyl-2-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-heptadecyl]-amide
  参考文献：
  名称：

  Effects of 3α- and 3β-galactosylated α-g galactosylceramides on the immune system

  摘要：

  We compared effects of a-galactosylceramide (alpha-GalCer) and its 3 alpha- or 3 beta-galactosylated derivatives on the proliferation of murine spleen cells. The 3 alpha-galactosylated alpha-GalCer showed stronger proliferative response than the parental alpha-GalCer, but the 3 beta-galactosylated alpha-GalCer possessed weaker activity than the alpha-GalCer. In addition, alpha-Gal-3-Cer did not show immunostimulatory activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00054-2
• 作为产物：
  描述：

  C14 二氢神经酰胺 、 乙酸酐 、 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl fluoride 在 silver perchlorate 、 三乙胺 、 tin(ll) chloride 作用下， 生成 Acetic acid (2S,3R)-2-tetradecanoylamino-3-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-octadecyl ester 、 Acetic acid (R)-1-[(S)-1-tetradecanoylamino-2-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadecyl ester
  参考文献：
  名称：

  Effects of 3α- and 3β-galactosylated α-g galactosylceramides on the immune system

  摘要：

  We compared effects of a-galactosylceramide (alpha-GalCer) and its 3 alpha- or 3 beta-galactosylated derivatives on the proliferation of murine spleen cells. The 3 alpha-galactosylated alpha-GalCer showed stronger proliferative response than the parental alpha-GalCer, but the 3 beta-galactosylated alpha-GalCer possessed weaker activity than the alpha-GalCer. In addition, alpha-Gal-3-Cer did not show immunostimulatory activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00054-2