2-(diphenylphosphonooxy)ethyl 3-O-<(R)-3-benzyloxytetradecanoyl>-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-6-O-<2-deoxy-4-O-diphenylphosphono-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-3-O-<(R)-3-(2,2,2-tr..)..>..>... | 118638-34-9

• 分子结构分类: 有机化合物
• 英文名称: 2-(diphenylphosphonooxy)ethyl 3-O-<(R)-3-benzyloxytetradecanoyl>-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-6-O-<2-deoxy-4-O-diphenylphosphono-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-3-O-<(R)-3-(2,2,2-tr..)..>..>...
• 英文别名: [(2S,3R,4R,5S,6R)-2-(2-diphenoxyphosphoryloxyethoxy)-6-[[(2R,3R,4R,5S,6R)-5-diphenoxyphosphoryloxy-3-(2,2,2-trichloroethoxycarbonylamino)-6-(2,2,2-trichloroethoxycarbonyloxymethyl)-4-[(3R)-3-(2,2,2-trichloroethoxycarbonyloxy)tetradecanoyl]oxyoxan-2-yl]oxymethyl]-5-hydroxy-3-[[(3R)-3-phenylmethoxytetradecanoyl]amino]oxan-4-yl] (3R)-3-phenylmethoxytetradecanoate
• CAS: 118638-34-9
• 化学式: C₁₀₃H₁₃₉Cl₉N₂O₂₈P₂
• 分子量: 2234.26
• InChiKey: DYCPYQMUYDUCIA-NUMNVVEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  27.06
• 重原子数：
  144.0
• 可旋转键数：
  70.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  356.22
• 氢给体数：
  3.0
• 氢受体数：
  28.0

反应信息

• 作为反应物：
  描述：

  2-(diphenylphosphonooxy)ethyl 3-O-<(R)-3-benzyloxytetradecanoyl>-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-6-O-<2-deoxy-4-O-diphenylphosphono-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-3-O-<(R)-3-(2,2,2-tr..)..>..>... 生成 2-(diphenylphosphonooxy)ethyl 3-O-<(R)-3-benzyloxytetradecanoyl>-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-6-O-<2-deoxy-4-O-diphenylphosphono-3-O-<(R)-3-hydroxytetradecanoyl>-2-<(R)-3-hydroxytetradecanoylamino>-β-D-glucopyranosyl>-α-D-glucopyra...
  参考文献：
  名称：

  KUSAMA, TSUNEO;SOGA, TSUNEHIKO;SHIBA, TETSUO

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(diphenylphosphonooxy)ethyl 3-O-<(R)-3-benzyloxytetradecanoyl>-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-α-D-glucopyranoside 生成 2-(diphenylphosphonooxy)ethyl 3-O-<(R)-3-benzyloxytetradecanoyl>-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-6-O-<2-deoxy-4-O-diphenylphosphono-6-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-3-O-<(R)-3-(2,2,2-tr..)..>..>...
  参考文献：
  名称：

  KUSAMA, TSUNEO;SOGA, TSUNEHIKO;SHIBA, TETSUO

  摘要：

  DOI：

文献信息

• Synthesis and Biological Activities of Analogs of a Lipid A Biosynthetic Precursor: 1-O-Phosphonooxyethyl-4'-O-phosphono-disaccharides with (R)-3-Hydroxytetradecanoyl or Tetradecanoyl Groups at Positions 2, 3, 2' and 3'.
  作者：Tsuneo KUSAMA、Tsunehiko SOGA、Yoshiyuki ONO、Eiji KUMAZAWA、Emiko SHIOYA、Yasuaki OSADA、Shoichi KUSUMOTO、Tetsuo SHIBA

  DOI：10.1248/cpb.39.1994

  日期：——

  Two novel analogs of a biosynthetic precursor of lipid A (2) were synthesized. The one analog (3) has acyl groups identical to those of 2, and the other (4) has tetradecanoyl groups in place of the (R)-3-hydroxytetradecanoyl groups of 2. Both 3 and 4 possess an alpha-glycosidically-bound phosphonooxyethyl group in place of the alpha-glycosyl phosphate group of 2. Compounds 3 and 4 exhibited definite

  合成了脂质A（2）的生物合成前体的两个新的类似物。一个类似物（3）的酰基与2的酰基相同，另一个类似物（4）的十四烷酰基代替2的（R）-3-羟基十四烷酰基。3和4均具有与糖苷键合的α磷酸氧代氧乙基取代了2的α-糖基磷酸基团。化合物3和4与原始化合物2一样，对Meth A纤维肉瘤表现出确定的抗肿瘤活性，并且对兔子的毒性低。用十四烷酰基取代羟基十四烷酰基几乎没有影响抗肿瘤活性，但是稍微增强了对兔子的毒性。