(2S,3R,4E)-3-hydroxy-2-(octadecanoylamino)octadec-4-enyl 2-acetylamino-2-deoxy-4-O-phosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: (2S,3R,4E)-3-hydroxy-2-(octadecanoylamino)octadec-4-enyl 2-acetylamino-2-deoxy-4-O-phosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-5-acetamido-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]-3-phosphonooxyoxan-4-yl] (3R)-3-tetradecanoyloxytetradecanoate
• 化学式: C₇₂H₁₃₇N₂O₁₄P
• 分子量: 1285.86
• InChiKey: UHENEZXTZVQDNJ-PTAPTVAJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  23
• 重原子数：
  89
• 可旋转键数：
  66
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  237
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  (2S,3R,4E)-3-hydroxy-2-(octadecanoylamino)octadec-4-enyl 2-acetylamino-2-deoxy-4-O-(diallylphosphono)-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranoside 在 四(三苯基膦)钯 甲酸 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以96%的产率得到(2S,3R,4E)-3-hydroxy-2-(octadecanoylamino)octadec-4-enyl 2-acetylamino-2-deoxy-4-O-phosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of ceramidated GLA-60 derivatives

  摘要：

  Ceramidated GLA-60 derivatives 11 and 11' were synthesized from I via glycosidation of ceramide derivative 12 as a glycosyl acceptor with GLA-60 derivative 5 as a glycosyl donor, and successive conversion. Compound 11' showed only weak LPS-antagonistic activity without showing any LPS-agonistic activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00179-9

文献信息

• Synthesis of ceramidated GLA-60 derivatives
  作者：Tsuyoshi Nakamura、Masao Shiozaki、Shin-ichi Kurakata

  DOI：10.1016/s0008-6215(02)00179-9

  日期：2002.9

  Ceramidated GLA-60 derivatives 11 and 11' were synthesized from I via glycosidation of ceramide derivative 12 as a glycosyl acceptor with GLA-60 derivative 5 as a glycosyl donor, and successive conversion. Compound 11' showed only weak LPS-antagonistic activity without showing any LPS-agonistic activity. (C) 2002 Elsevier Science Ltd. All rights reserved.