(5S)-methyl 8-(dimethylphosphono)-5-<(tert-butyldiphenylsilyl)oxy>-6-octynoate | 148519-78-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (5S)-methyl 8-(dimethylphosphono)-5-<(tert-butyldiphenylsilyl)oxy>-6-octynoate
• 英文别名: methyl (5S)-5-[tert-butyl(diphenyl)silyl]oxy-8-dimethoxyphosphoryloct-6-ynoate
• CAS: 148519-78-2
• 化学式: C₂₇H₃₇O₆PSi
• 分子量: 516.646
• InChiKey: KCOTZJIYMSRNGV-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.76
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5S)-methyl 8-(dimethylphosphono)-5-<(tert-butyldiphenylsilyl)oxy>-6-octynoate 在 10% palladium on barium sulfate 吡啶 、 喹啉 、 lithium hydroxide 、 氢氟酸 、 四丁基氟化铵 、 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 异丙醇 为溶剂， 反应 33.0h， 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：

  4-氯甲酰基丁酸甲酯 在 咪唑 、 正丁基锂 、 (-)-(S)-alpine-borane 、 溴 、 sodium hexamethyldisilazane 、 1,2-双(二苯基膦)乙烷 、 copper(l) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.91h， 生成 (5S)-methyl 8-(dimethylphosphono)-5-<(tert-butyldiphenylsilyl)oxy>-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
• 作为试剂：
  描述：

  (2E,4R)-(tert-Butyldiphenylsilyloxy)dodec-2-en-6-ynal 、 (5S)-methyl 8-(dimethylphosphono)-5-<(tert-butyldiphenylsilyl)oxy>-6-octynoate 在 (5S)-methyl 8-(dimethylphosphono)-5-<(tert-butyldiphenylsilyl)oxy>-6-octynoate 作用下， 以77的产率得到(8E,10E)-methyl 5(S),12(R)-bis(tert-butyldiphenylsiloxy)eicosa-8,10-diene-14,16-diynoate
  参考文献：
  名称：

  J. Org. Chem. 1993, 58, 3516-3520

  摘要：

  DOI：

文献信息

• Total synthesis of leukotriene B4
  作者：Francis A. J. Kerdesky、Steven P. Schmidt、Dee W. Brooks

  DOI：10.1021/jo00065a012

  日期：1993.6

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

  DOI：——

  日期：——