3(R)-hydroxyleukotriene B₄ methyl ester | 157478-55-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3(R)-hydroxyleukotriene B₄ methyl ester
• 英文别名: methyl (3R,5S,6Z,8E,10E,12R,14Z)-3,5,12-trihydroxyicosa-6,8,10,14-tetraenoate
• CAS: 157478-55-2
• 化学式: C₂₁H₃₄O₅
• 分子量: 366.498
• InChiKey: XSZLTHVRCMHKRZ-WSIYOMMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  26.0
• 可旋转键数：
  14.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  86.99
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3(R)-hydroxyleukotriene B₄ methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以95%的产率得到3(R)-hydroxy-leulotriene B4
  参考文献：
  名称：

  Total synthesis of the ethanol inducible, proinflammatory autacoid 3(S)-hydroxy-leukotriene B4 (3-OH-LTB4) and analogues

  摘要：

  3(S)-Hydroxy-Leukotriene B-4 (1a), its 3(R)-epimer 1b, and a 14,15-acetylenic analogue were efficiently prepared via chelation-controlled reduction of ketone 12, obtained by acetylide addition to chiral beta-hydroxylactones 7/9.

  DOI：

  10.1016/s0040-4039(00)73170-4
• 作为产物：
  描述：

  (8E,10E,14Z)-(3R,5S,12R)-3,5,12-Trihydroxy-icosa-8,10,14-trien-6-ynoic acid methyl ester 在 锌 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 以67%的产率得到3(R)-hydroxyleukotriene B₄ methyl ester
  参考文献：
  名称：

  Total synthesis of the ethanol inducible, proinflammatory autacoid 3(S)-hydroxy-leukotriene B4 (3-OH-LTB4) and analogues

  摘要：

  3(S)-Hydroxy-Leukotriene B-4 (1a), its 3(R)-epimer 1b, and a 14,15-acetylenic analogue were efficiently prepared via chelation-controlled reduction of ketone 12, obtained by acetylide addition to chiral beta-hydroxylactones 7/9.

  DOI：

  10.1016/s0040-4039(00)73170-4

文献信息

• 3-Hydroxyleukotriene B4 (3-OH-LTB4): Total Synthesis and Stereochemical Assignment.
  作者：Rama K. Bhatt、Kamlesh Chauhan、Pat Wheelan、J. R. Falck、Robert C. Murphy

  DOI：10.1021/ja00091a004

  日期：1994.6

  The asymmetric total synthesis of 3-hydroxyleukotriene B-4 (3-OH-LTB(4)), an ethanol-inducible proinflammatory autacoid, was achieved using a triply convergent strategy for the sequential union of propargylic arsonium salt 3 with pyranosides 2a,b and furanose 4. Both saccharide subunits were derived from commercial 2-deoxy-D-ribose. The key transformation involved palladium-mediated coupling of bromoacetylenide 9 with stannylglycal 6a,b. Subsequent Rieke zinc hydrogenation of acetylene 10a,b and controlled ionic reduction of the cross-conjugated cyclic enol ether using NaBH3CN at pH similar to 4-4.5 established the cis-Delta(6,7)-olefin and C(5)-hydroxyl stereochemistry, respectively, and led to 11a,b. Methyllactol hydrolysis, PCC oxidation, methanolysis, and desilylation afforded 3(R)- and 3(S)-OH-LTB(4) methyl esters, respectively. On the basis of chromatographic and mass spectral comparisons, enzymatically derived 3-OH-LTB(4) is composed principally of the 3(S)-isomer (>95%).