2-(4-bromophenyl)-2-oxoethyl (R)-3-benzyloxyhexadecanoate | 548486-24-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-bromophenyl)-2-oxoethyl (R)-3-benzyloxyhexadecanoate
• 英文别名: 2-(4-bromophenyl)-2-oxoethyl (R)-3-benzyloxyhexadecanoate
• CAS: 548486-24-4
• 化学式: C₃₁H₄₃BrO₄
• 分子量: 559.584
• InChiKey: AJFCMWXTIIIUMC-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.85
• 重原子数：
  36.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(4-bromophenyl)-2-oxoethyl (R)-3-benzyloxyhexadecanoate 在 N,N'-二环己基碳二亚胺 、 锌 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 18.0h， 生成 4-oxo-pentanoic acid 1-({6-[3-benzyloxy-5-(3-benzyloxy-hexadecanoylamino)-4-hydroxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy]-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ylcarbamoyl}-methyl)-tetradecyl ester
  参考文献：
  名称：

  Preparation of a Lipid A Derivative That Contains a 27-Hydroxyoctacosanoic Acid Moiety

  摘要：

  A general synthetic strategy for long-chain omega-1 hydroxy fatty acids has been developed, which employs as a key reaction step a cross metathesis between omega-unsaturated ester and 3-butene-2-ol. The resulting lipids were used for the preparation of lipid A derivatives of Rhizobium sin-1, which have the ability to inhibit the E. coli LPS-dependent synthesis of tumor necrosis factor by human monocytes.

  DOI：

  10.1021/ol048746f
• 作为产物：
  描述：

  2,2,2-三氯乙酰胺苄酯 、 2-(4-bromophenyl)-2-oxoethyl (R)-3-hydroxyhexadecanoate 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以88%的产率得到2-(4-bromophenyl)-2-oxoethyl (R)-3-benzyloxyhexadecanoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Rhizobium sin-1 Lipid A Derivatives

  摘要：

  A highly convergent strategy for the synthesis of several derivatives of the lipid A of Rhizobium sin-1 has been developed. The approach employed the advanced intermediate 3-O-acetyl-6-O-(3-O-acetyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-beta-D-glucopyrano-syl)-2-azido-4-O-benzyl-2-deoxy-1 -thio-alpha-D-glucopyranoside (5), which is protected in such a way that the anomeric center, the C-2 and C-2' amino groups, and the C-3 and C-3' hydroxyls can be selectively functionalized. The synthetic strategy was used for the preparation of 2-deoxy-6-O-12-deoxy-3-O-[(R)-3-hydroxy-hexadecanoyl]-2-[(R)-3-octacosanoyloxy-hexadecan]amido-beta-D-glucopyranosyl}-2-[(R)-3-hydroxy-hexadecan]amido-3-O-[(R)-3-hydroxy-hexadecanoyl]- alpha-D-glucopyranose (11) and 2-deoxy-6-O-{2-deoxy-3-O[(R)-3-hydroxy-hexadecanoyl]-2-[(R)-3-octacosanoyloxy-hexadecan]amido-D-glucopyranosyl}-2-[(R)-3-hydroxy-hexadecan]amido-3-O-[(R)-3-hydroxy-hexadecanoyl]-D-glucono-1,5-lactone (13), which contain an unusual octacosanoic acid moiety and differ in the oxidation state of the anomeric center. The results of biological studies indicate that 11 and 13 lack the proinflammatory effects of Escherichia coli lipopolysaccharicles (LPS). Furthermore, 13 emulated the ability of heterogeneous R. sin-1 LPS to antagonize enteric LPS, providing evidence for the critical role of the gluconolactone moiety of R. sin-1 LPS in mediating this antagonistic effect. Compound 13 is the first example of a lipid A derivative that is devoid of phosphate but possesses antagonistic properties, making it an attractive lead compound for development of a drug to use in the treatment of Gram-negative septicemia.

  DOI：

  10.1021/ja029316s