(2S,3S,4R)-2-amino-3,4-di-O-benzyl-1-O-[2,3,4-tri-O-benzyl-6-O-(2-benzyloxyethyl)-α-D-galactopyranosyl]octadecane-1,3,4-triol | 1435266-74-2

• 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,3S,4R)-2-amino-3,4-di-O-benzyl-1-O-[2,3,4-tri-O-benzyl-6-O-(2-benzyloxyethyl)-α-D-galactopyranosyl]octadecane-1,3,4-triol
• CAS: 1435266-74-2
• 化学式: C₆₈H₈₉NO₉
• 分子量: 1064.46
• InChiKey: VVOCIBNIVLLDTA-BXLGKZHKSA-N

物化性质

• 沸点：
  993.9±65.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.31
• 重原子数：
  78.0
• 可旋转键数：
  40.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  109.09
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  hexacosanoyl chloride 、 (2S,3S,4R)-2-amino-3,4-di-O-benzyl-1-O-[2,3,4-tri-O-benzyl-6-O-(2-benzyloxyethyl)-α-D-galactopyranosyl]octadecane-1,3,4-triol 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以81%的产率得到(2S,3S,4R)-3,4-di-O-benzyl-2-hexacosanamido-1-O-[2,3,4-tri-O-benzyl-6-O-(2-benzyloxyethyl)-α-D-galactopyranosyl]octadecane-1,3,4-triol
  参考文献：
  名称：

  RCAI-61 and related 6′-modified analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo

  摘要：

  We synthesized ten new analogs of 6'-modified KRN7000 (A): RCAI-58, 61, 64, 83, 85-87, 113, 119, and 125. They could be synthesized by alpha-selective galactosylation of ceramide 9 with the 6-modified D-galactopyranosyl fluorides (8a-8f) or L-arabinopyranosyl fluoride (17), or by etherification of the known alcohol 19. Bioassay of the ten analogs demonstrated that RCAI-61 (1, 6'-O-methylated analog of A) was the most potent immunostimulant among them, and could induce the production of a large amount of IFN-gamma even at a low concentration in mice in vivo. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.028
• 作为产物：
  描述：

  (2S,3S,4R)-2-azido-3,4-di-O-benzyl-1-O-[2,3,4-tri-O-benzyl-6-O-(2-benzyloxyethyl)-α-D-galactopyranosyl]octadecane-1,3,4-triol 在 三甲基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 22.0h， 以78%的产率得到(2S,3S,4R)-2-amino-3,4-di-O-benzyl-1-O-[2,3,4-tri-O-benzyl-6-O-(2-benzyloxyethyl)-α-D-galactopyranosyl]octadecane-1,3,4-triol
  参考文献：
  名称：

  RCAI-61 and related 6′-modified analogs of KRN7000: Their synthesis and bioactivity for mouse lymphocytes to produce interferon-γ in vivo

  摘要：

  We synthesized ten new analogs of 6'-modified KRN7000 (A): RCAI-58, 61, 64, 83, 85-87, 113, 119, and 125. They could be synthesized by alpha-selective galactosylation of ceramide 9 with the 6-modified D-galactopyranosyl fluorides (8a-8f) or L-arabinopyranosyl fluoride (17), or by etherification of the known alcohol 19. Bioassay of the ten analogs demonstrated that RCAI-61 (1, 6'-O-methylated analog of A) was the most potent immunostimulant among them, and could induce the production of a large amount of IFN-gamma even at a low concentration in mice in vivo. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.028