(2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynyl 4-nitrobenzoate | 148519-84-0

• 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: (2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynyl 4-nitrobenzoate
• 英文别名: [(2R)-2-[tert-butyl(diphenyl)silyl]oxydec-4-ynyl] 4-nitrobenzoate
• CAS: 148519-84-0
• 化学式: C₃₃H₃₉NO₅Si
• 分子量: 557.762
• InChiKey: QWKGMOHBPMKNRW-GDLZYMKVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynyl 4-nitrobenzoate 在 10% palladium on barium sulfate 吡啶 、 喹啉 、 lithium hydroxide 、 四丙基高钌酸铵 、 4 A molecular sieve 、 氢氟酸 、 四丁基氟化铵 、 氢气 、 N-甲基吗啉氧化物 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 异丙醇 、 苯 为溶剂， 反应 48.0h， 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：

  1-庚炔 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynyl 4-nitrobenzoate
  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：——
• 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.