(2S,3S,4R)-1-O-[6-O-(2-methoxyethoxymethyl)-α-D-galactopyranosyl]-2-(hexacosanamido)octadecane-1,3,4-triol | 1435267-32-5

• 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)-1-O-[6-O-(2-methoxyethoxymethyl)-α-D-galactopyranosyl]-2-(hexacosanamido)octadecane-1,3,4-triol
• 英文别名: RCAI-119；N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(2-methoxyethoxymethoxymethyl)oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
• CAS: 1435267-32-5
• 化学式: C₅₄H₁₀₇NO₁₁
• 分子量: 946.444
• InChiKey: IMJYQJUHWATMGW-WFMKRGBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.8
• 重原子数：
  66
• 可旋转键数：
  50
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  176
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  (2S,3S,4R)-3,4-di-O-benzyl-2-hexacosanamido-1-O-[2,3,4-tri-O-benzyl-6-O-(2-methoxyethoxymethyl)-α-D-galactopyranosyl]octadecane-1,3,4-triol 在 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以55%的产率得到(2S,3S,4R)-1-O-[6-O-(2-methoxyethoxymethyl)-α-D-galactopyranosyl]-2-(hexacosanamido)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