(2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynal | 90108-26-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynal
• 英文别名: (2R)-2-(tert-Butyldiphenylsilyloxy)dec-4-ynal；(2R)-2-[tert-butyl(diphenyl)silyl]oxydec-4-ynal
• CAS: 90108-26-2
• 化学式: C₂₆H₃₄O₂Si
• 分子量: 406.64
• InChiKey: RAFRCDPQXRVDKW-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynal 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 、 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：

  (2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynyl 4-nitrobenzoate 在 lithium hydroxide 、 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decynal
  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

• Synthesis of (2E,4E)-dienals by double formyl-olefination with an arsonium salt and its application in the syntheses of lipoxygenase metabolites of arachidonic acid
  作者：Zhi-Hui Peng、Yun-Long Li、Wen-Lian Wu、Cui-Xian Liu、Yu-Lin Wu

  DOI：10.1039/p19960001057

  日期：——

  A new facile route to (2E,4E)-dienals by a double formyl-olefination with arsonium salts has been developed. By this method and with other arsonium reagents in the key step some lipoxygenase metabolites of arachidonic acid, lipoxin A4 and B4 and leukotriene B4, have been synthesized.

  已开发出一种新的简便方法，该方法通过用ar盐进行双甲酰基-烯化来实现（2 E，4 E）二烯。通过该方法以及在关键步骤中与其他砷试剂一起，合成了花生四烯酸，脂蛋白A 4和B 4以及白三烯B 4的一些脂氧合酶代谢产物。
• Total enantiospecific synthesis of 12(r)-hete
  作者：Ira M. Taffer、Robert E. Zipkin

  DOI：10.1016/s0040-4039(00)96908-9

  日期：——

  A total synthesis of 12(R)-hydroxy-5,8,14--10--eicosatetraenoic acid[12(R)-HETE] was accomplished via a short, efficient, enantiospecific route.

  的12（R）共合成羟基- 5,8,14- -10- -eicosatetraenoic甲酸[12（R）-HETE]已通过短，效率高，对映体特异性的路线来实现。
• A general and stereocontrolled total synthesis of leukotriene B4 and analogs
  作者：K. C. Nicolaou、R. E. Zipkin、R. E. Dolle、B. D. Harris

  DOI：10.1021/ja00324a024

  日期：1984.6
• Total synthesis of the ethanol inducible, proinflammatory autacoid 3(S)-hydroxy-leukotriene B4 (3-OH-LTB4) and analogues
  作者：Kamlesh Chauhan、Rama K. Bhatt、J.R. Falck、Jorge H. Capdevila

  DOI：10.1016/s0040-4039(00)73170-4

  日期：1994.3

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

  DOI：——

  日期：——