(5S)-methyl 5-<(tert-butyldiphenylsilyl)oxy>-8-(tetrahydropyran-2-yloxy)-6-octynoate

• 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: (5S)-methyl 5-<(tert-butyldiphenylsilyl)oxy>-8-(tetrahydropyran-2-yloxy)-6-octynoate
• 英文别名: methyl (5S)-5-[tert-butyl(diphenyl)silyl]oxy-8-(oxan-2-yloxy)oct-6-ynoate
• 化学式: C₃₀H₄₀O₅Si
• 分子量: 508.73
• InChiKey: QPIBSOGUUOOSMN-GMMLNUAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S)-methyl 5-<(tert-butyldiphenylsilyl)oxy>-8-(tetrahydropyran-2-yloxy)-6-octynoate 在 10% palladium on barium sulfate 喹啉 、 四丁基氟化铵 、 氢气 、 溴 、 sodium hexamethyldisilazane 、 1,2-双(二苯基膦)乙烷 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 23.33h， 生成 白三烯B4
  参考文献：
  名称：

  Total synthesis of leukotriene B4

  摘要：

  A new, efficient, and stereocontrolled total synthesis of leukotriene B4 (1) has been developed. The convergent route employs a stereospecific Horner-Wadsworth-Emmons coupling of propargylic phosphonate 2 and aldehyde 3 to provide the essential carbon framework in 77% yield. The requisite phosphonate 2 containing the C1-C8 fragment was readily prepared in 47% yield from methyl 4-(chloroformyl)butyrate via an enantioselective reduction of alcohol 4 while the chiral aldehyde 3 which comprises the C9-C20 skeleton of the eicosanoid was synthesized in 52% yield from optically active (2R)-(-)-glycidyl 4-nitrobenzoate.

  DOI：

  10.1021/jo00065a012
• 作为产物：
  描述：

  methyl 5-oxo-8-(tetrahydropyran-2-yloxy)-6-octynoate 在 咪唑 、 (-)-(S)-alpine-borane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 (5S)-methyl 5-<(tert-butyldiphenylsilyl)oxy>-8-(tetrahydropyran-2-yloxy)-6-octynoate
  参考文献：
  名称：

  Total synthesis of leukotriene B4

  摘要：

  A new, efficient, and stereocontrolled total synthesis of leukotriene B4 (1) has been developed. The convergent route employs a stereospecific Horner-Wadsworth-Emmons coupling of propargylic phosphonate 2 and aldehyde 3 to provide the essential carbon framework in 77% yield. The requisite phosphonate 2 containing the C1-C8 fragment was readily prepared in 47% yield from methyl 4-(chloroformyl)butyrate via an enantioselective reduction of alcohol 4 while the chiral aldehyde 3 which comprises the C9-C20 skeleton of the eicosanoid was synthesized in 52% yield from optically active (2R)-(-)-glycidyl 4-nitrobenzoate.

  DOI：

  10.1021/jo00065a012

文献信息

• J. Org. Chem. 1993, 58, 3516-3520
  作者：

  DOI：——

  日期：——