(2S,3S,4R)-1-{N-[β-galactosylpyranosyl-(1→4)-β-glucopyranosyl]-N-methoxyamino}-2-[N-octadecanoylamino]octadecane-3,4-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,3S,4R)-1-{N-[β-galactosylpyranosyl-(1→4)-β-glucopyranosyl]-N-methoxyamino}-2-[N-octadecanoylamino]octadecane-3,4-diol
• 化学式: C₄₉H₉₆N₂O₁₄
• 分子量: 937.306
• InChiKey: ZIHUOCVIOGTYGK-JOYPRMQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  65.0
• 可旋转键数：
  40.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  251.33
• 氢给体数：
  10.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  (2S,3S,4R)-2-[N-(9-fluorenylmethyloxycarbonyl)amino]-1-[N-methoxy-N-octadecanoylamino]octadecane-3,4-diol 在 哌啶 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 为溶剂， 反应 75.0h， 生成 (2S,3S,4R)-1-{N-[β-galactosylpyranosyl-(1→4)-β-glucopyranosyl]-N-methoxyamino}-2-[N-octadecanoylamino]octadecane-3,4-diol
  参考文献：
  名称：

  Synthesis of neoglycosphingolipid from methoxyamino-functionalized ceramide

  摘要：

  An efficient approach for the synthesis of a methoxyamino- functionalized ceramide was established from phytosphingosine using specific Nb -> Na acyl migration of the octadecanoyl group during the removal of Na-Fmoc protective group. One step glycoblotting reaction of the ceramide mimic with lactose afforded a neoglycosphingolipid showing potent inhibitory activity against recombinant endoglycoceramidase II from Rhodococcus sp. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.091

文献信息

• Synthesis of neoglycosphingolipid from methoxyamino-functionalized ceramide
  作者：Junya Ishida、Hiroshi Hinou、Kentaro Naruchi、Shin-Ichiro Nishimura

  DOI：10.1016/j.bmcl.2013.12.091

  日期：2014.2

  An efficient approach for the synthesis of a methoxyamino- functionalized ceramide was established from phytosphingosine using specific Nb -> Na acyl migration of the octadecanoyl group during the removal of Na-Fmoc protective group. One step glycoblotting reaction of the ceramide mimic with lactose afforded a neoglycosphingolipid showing potent inhibitory activity against recombinant endoglycoceramidase II from Rhodococcus sp. (C) 2014 Elsevier Ltd. All rights reserved.