(2S,3R,4E)-2-amino-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-N-acetyl-4-octadecene-1,3-diol

• 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,4E)-2-amino-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-N-acetyl-4-octadecene-1,3-diol
• 英文别名: N-[(E,2S,3R)-3-hydroxy-1-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoctadec-4-en-2-yl]acetamide
• 化学式: C₅₄H₇₃NO₈
• 分子量: 864.176
• InChiKey: TWSIOHKKJSPUER-XDYYVMDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.5
• 重原子数：
  63
• 可旋转键数：
  31
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3R,4E)-2-amino-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-N-acetyl-4-octadecene-1,3-diol 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以73%的产率得到(2S,3R,4E)-2-amino-1-O-(α-D-galactopyranosyl)-N-acetyl-4-octadecene-1,3-diol
  参考文献：
  名称：

  Effects of α- and β-Galactosylated C2-Ceramides on the Immune System

  摘要：

  In contrast to the immunosuppressive effects of C2-ceramide (C2-Cer), alpha-galactosylceramides with ceramides having more than 10 carbons in fatty acid chains have immunostimulatory activities. We therefore synthesized alpha- and beta-galactosylated C2-Cers in order to examine their effects on the immune system. beta-Galactosylated C2-Cer and Ca-Cer suppressed the allogeneic mixed leukocyte reaction (MLR) responses, but alpha-galactosylated C2-Cer stimulated the MLR response.

  DOI：

  10.1021/jm970613v
• 作为产物：
  描述：

  N-乙酰基神经鞘氨醇 、 2,3,4,6-tetra-O-benzyl-D-galactopyranosyl fluoride 在 4 A molecular sieve 、 silver perchlorate 、 tin(ll) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以23%的产率得到(2S,3R,4E)-2-amino-1-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-N-acetyl-4-octadecene-1,3-diol
  参考文献：
  名称：

  Effects of α- and β-Galactosylated C2-Ceramides on the Immune System

  摘要：

  In contrast to the immunosuppressive effects of C2-ceramide (C2-Cer), alpha-galactosylceramides with ceramides having more than 10 carbons in fatty acid chains have immunostimulatory activities. We therefore synthesized alpha- and beta-galactosylated C2-Cers in order to examine their effects on the immune system. beta-Galactosylated C2-Cer and Ca-Cer suppressed the allogeneic mixed leukocyte reaction (MLR) responses, but alpha-galactosylated C2-Cer stimulated the MLR response.

  DOI：

  10.1021/jm970613v

文献信息

• Effects of α- and β-Galactosylated C2-Ceramides on the Immune System
  作者：Teruyuki Sakai、Hitomi Ueno、Takenori Natori、Akira Uchimura、Kazuhiro Motoki、Yasuhiko Koezuka

  DOI：10.1021/jm970613v

  日期：1998.2.1

  In contrast to the immunosuppressive effects of C2-ceramide (C2-Cer), alpha-galactosylceramides with ceramides having more than 10 carbons in fatty acid chains have immunostimulatory activities. We therefore synthesized alpha- and beta-galactosylated C2-Cers in order to examine their effects on the immune system. beta-Galactosylated C2-Cer and Ca-Cer suppressed the allogeneic mixed leukocyte reaction (MLR) responses, but alpha-galactosylated C2-Cer stimulated the MLR response.