benzyl (R)-3-hydroxytetradecanoate | 88862-84-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (R)-3-hydroxytetradecanoate
• 英文别名: benzyl (3R)-3-hydroxytetradecanoate
• CAS: 88862-84-4
• 化学式: C₂₁H₃₄O₃
• 分子量: 334.499
• InChiKey: NRNRXBHTCKDUNQ-HXUWFJFHSA-N

物化性质

• 沸点：
  458.2±20.0 °C(Predicted)
• 密度：
  0.989±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (R)-3-hydroxytetradecanoate 在 5%-palladium/activated carbon 氢气 、 sodium acetate 、 对甲苯磺酸 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 1,1,3,3-四甲基脲 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 氯仿 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 120.0 ℃ 、5.0 MPa 条件下， 反应 10.5h， 生成
  参考文献：
  名称：

  Charon, Daniel; Mondange, Michelle; Szabo, Ladislas, Journal of the Chemical Society. Perkin transactions I, 1984, # 10, p. 2291 - 2296

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-3-羟基肉豆蔻酸甲酯 在 sodium hydroxide 、 四丁基碘化铵 、 三乙胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 18.0h， 生成 benzyl (R)-3-hydroxytetradecanoate
  参考文献：
  名称：

  Synthesis and Immunobiological Activity of an Original Series of Acyclic Lipid A Mimics Based on a Pseudodipeptide Backbone

  摘要：

  N-delta-L-Homoserinyl-D-ornithinol pseudodipeptides N-acylated with typical Escherichia coli lipid A fatty acid residues and mono-O- or bis-O-phosphorylated have been prepared and their properties investigated. The derivatives carrying two phosphate groups were found to be inducers of NO production. In addition, while they were unable to induce significantly the production of interleukin-6 (IL-6) by human PBMC cells, these compounds behaved also as potent antagonists of LPS-induced IL-6 production in the same human cells system. In conclusion, the molecules described here are the first members of an original class of immunobiologically active lipid A mimics based on an acyclic pseudodipeptide backbone carrying only the essential functionalities of the parent lipid A structure (OM-174). As the products exhibit very low endotoxicity and pyrogenicity, this class of lipid A mimics therefore opens a new generation of immunoadjuvants that possibly could reach clinical applications.

  DOI：

  10.1021/jm060482a

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。
• Sakai, Naoko; Ageishi, Satoru; Isobe, Hiroshi, Journal of the Chemical Society. Perkin transactions I, 2000, # 1, p. 71 - 78
  作者：Sakai, Naoko、Ageishi, Satoru、Isobe, Hiroshi、Hayashi, Yoshiyuki、Yamamoto, Yukio

  DOI：——

  日期：——
• Synthesis of O-{2-deoxy-2-[(3R)-3-hydroxytetradecanamido]-β-d-glucopyranosyl 4-phosphate}-(1→6)-2-deoxy-2-[(3R)-3-hydroxytetradecanamido]-d-glucose. The disaccharide route
  作者：Daniel Charon、Ladislas Szabó

  DOI：10.1016/0008-6215(83)88321-9

  日期：1983.1
• Synthesis and Immunobiological Activity of an Original Series of Acyclic Lipid A Mimics Based on a Pseudodipeptide Backbone
  作者：Olivier R. Martin、Wei Zhou、Xinfu Wu、Sophie Front-Deschamps、Stéphane Moutel、Katharina Schindl、Patricia Jeandet、Claude Zbaeren、Jacques A. Bauer

  DOI：10.1021/jm060482a

  日期：2006.10.1

  N-delta-L-Homoserinyl-D-ornithinol pseudodipeptides N-acylated with typical Escherichia coli lipid A fatty acid residues and mono-O- or bis-O-phosphorylated have been prepared and their properties investigated. The derivatives carrying two phosphate groups were found to be inducers of NO production. In addition, while they were unable to induce significantly the production of interleukin-6 (IL-6) by human PBMC cells, these compounds behaved also as potent antagonists of LPS-induced IL-6 production in the same human cells system. In conclusion, the molecules described here are the first members of an original class of immunobiologically active lipid A mimics based on an acyclic pseudodipeptide backbone carrying only the essential functionalities of the parent lipid A structure (OM-174). As the products exhibit very low endotoxicity and pyrogenicity, this class of lipid A mimics therefore opens a new generation of immunoadjuvants that possibly could reach clinical applications.
• Charon, Daniel; Mondange, Michelle; Szabo, Ladislas, Journal of the Chemical Society. Perkin transactions I, 1984, # 10, p. 2291 - 2296
  作者：Charon, Daniel、Mondange, Michelle、Szabo, Ladislas

  DOI：——

  日期：——