(2R,3S)-(Z)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-undecene-1,2,3-triol | 95646-05-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S)-(Z)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-undecene-1,2,3-triol
• 英文别名: 3(S)-<(tert-butyldiphenylsilyl)oxy>-1,2-bis-O-(isopropylidene)-5(Z)-undecene-1,2(R)-diol；3-O-(tert-butyldiphenylsilyl)-1,2-bis-O-(1-methylethylidene)-5(Z)-undecene-1,2(R),3(S)-triol；tert-butyl-[(Z,1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]non-3-enoxy]-diphenylsilane
• CAS: 95646-05-2
• 化学式: C₃₀H₄₄O₃Si
• 分子量: 480.763
• InChiKey: JEXHFKJPFUJPPZ-ZSTHOZFYSA-N

物化性质

• 沸点：
  512.4±50.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-(Z)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-undecene-1,2,3-triol 在 lead(IV) acetate 、 lithium hydroxide 、 四丁基氟化铵 、 碳酸氢钠 、 sodium carbonate 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 5.25h， 生成 12(S-羟基(5Z,8Z,10E,14Z-二十四碳四烯酸
  参考文献：
  名称：

  The total synthesis of 12-HETE (12-hydroxyeicosatetraenoic acid) and 12,20-diHETE

  摘要：

  DOI：

  10.1021/jo00356a004
• 作为产物：
  描述：

  2,3:4,5-di-O-isopropylidene-D-arabinose diethyldithioacetal 在 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 sodium hexamethyldisilazane 、 silver nitrate 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙腈 为溶剂， 反应 45.42h， 生成 (2R,3S)-(Z)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-undecene-1,2,3-triol
  参考文献：
  名称：

  Cyclopropane-Containing Eicosanoids of Marine Origin. Biomimetic Synthesis of Constanolactones A and B from the Alga Constantinea simplex

  摘要：

  Asymmetric syntheses of 7, a substance isolated from incubation of arachidonic acid with an acetone powder of the coral Plexaura homomalla, and of constanolactones A (9) and B (10), metabolites of the red alga Constantinea simplex, are described. The key step involves stannic chloride-mediated cyclization of the oxirane derived from Sharpless epoxidation of 10-hydroxy-5,8-decadienoates, and is shown to yield a trans disubstituted cyclopropane Linked to a delta-lactone. Both (R) and (S) configurations at C5 of the lactone are produced in the cyclization, the ratio being independent of olefin geometry in the acyclic precursor, Elaboration of the cyclization products via Nozaki-Kishi coupling of the derived aldehydes 26 and 37 with the appropriate (1E,5Z)-1-iodo-1,5-undecadiene led to 7, 9, and 10, thereby establishing the relative configuration of 7 and confirming the absolute configuration of 9 and 10.

  DOI：

  10.1021/ja00128a008

文献信息

• Simple efficient synthesis of LTB4 and 12-epi-LTB4
  作者：Robert Zamboni、Joshua Rokach

  DOI：10.1016/s0040-4039(00)87415-8

  日期：1982.1
• The Total Synthesis of 5-Oxo-12(<i>S</i>)-hydroxy-6(<i>E</i>),8(<i>Z</i>),10(<i>E</i>),14(<i>Z</i>)-eicosatetraenoic Acid and Its 8,9-<i>trans</i>-Isomer and Their Identification in Human Platelets
  作者：Subhash P. Khanapure、William S. Powell、Joshua Rokach

  DOI：10.1021/jo9813282

  日期：1998.11.1

  The first total synthesis of 5-oxo-12(S)-hydroxy-6(E),8(Z),10(E), 14(Z)-eicosatetraenoic acid (5-oxo-12-HETE) 6 and its 8-trans-isomer 7 is reported. The synthetic 5-oxo-12-HETE 6 and its 8,9-trans-isomer 7 were used to identify their formation in mixtures of platelets and neutrophils by transcellular metabolism.
• Stereospecific synthesis of 11S, 12S-oxido 5Z, 7E, 9E, 14Z-eicosatetraenoic acid
  作者：Robert Zamboni、Suzanne Milette、Joshua Rokach

  DOI：10.1016/s0040-4039(01)81698-1

  日期：1984.1
• The total synthesis of 12-HETE (12-hydroxyeicosatetraenoic acid) and 12,20-diHETE
  作者：Yves Leblanc、Brian J. Fitzsimmons、Julian Adams、Francoise Perez、Joshua Rokach

  DOI：10.1021/jo00356a004

  日期：1986.3
• Cyclopropane-Containing Eicosanoids of Marine Origin. Biomimetic Synthesis of Constanolactones A and B from the Alga Constantinea simplex
  作者：James D. White、Mark S. Jensen

  DOI：10.1021/ja00128a008

  日期：1995.6

  Asymmetric syntheses of 7, a substance isolated from incubation of arachidonic acid with an acetone powder of the coral Plexaura homomalla, and of constanolactones A (9) and B (10), metabolites of the red alga Constantinea simplex, are described. The key step involves stannic chloride-mediated cyclization of the oxirane derived from Sharpless epoxidation of 10-hydroxy-5,8-decadienoates, and is shown to yield a trans disubstituted cyclopropane Linked to a delta-lactone. Both (R) and (S) configurations at C5 of the lactone are produced in the cyclization, the ratio being independent of olefin geometry in the acyclic precursor, Elaboration of the cyclization products via Nozaki-Kishi coupling of the derived aldehydes 26 and 37 with the appropriate (1E,5Z)-1-iodo-1,5-undecadiene led to 7, 9, and 10, thereby establishing the relative configuration of 7 and confirming the absolute configuration of 9 and 10.