ethyl (2Z,4S,5S,6E)-7-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(tritylioxy)ethyl]-[1,3]dioxolan-4-yl}-4-ethyl-5-hydroxyhepta-2,6-dienoate | 521274-28-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: ethyl (2Z,4S,5S,6E)-7-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(tritylioxy)ethyl]-[1,3]dioxolan-4-yl}-4-ethyl-5-hydroxyhepta-2,6-dienoate
• 英文别名: ethyl (2Z,4S,5S,6E)-7-[(2R,4R,5R)-2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-5-prop-2-enyl-4-(2-trityloxyethyl)-1,3-dioxolan-4-yl]-4-ethyl-5-hydroxyhepta-2,6-dienoate
• CAS: 521274-28-2
• 化学式: C₅₀H₆₂O₇Si
• 分子量: 803.124
• InChiKey: NVGSJKUEWIQUQE-DCJWZHNSSA-N

物化性质

• 沸点：
  795.2±60.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.26
• 重原子数：
  58
• 可旋转键数：
  21
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl (2Z,4S,5S,6E)-7-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(tritylioxy)ethyl]-[1,3]dioxolan-4-yl}-4-ethyl-5-hydroxyhepta-2,6-dienoate 在 碳酸氢钠 titanium(IV) isopropylate 、 potassium osmate(VI) 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 、 苯 为溶剂， 反应 98.25h， 生成 (5S,6S)-6-((E)-2-{(2R,4R,5R)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-5-(2,3-dihydroxypropyl)-4-[2-(trityloxy)ethyl]-[1,3]dioxolan-4-yl}vinyl)-5-ethyl-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Total Synthesis of Leustroducsin B

  摘要：

  A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrization of meso-diol 4 (90.2% ee) and preparation of the C9-C11 anti-diol moiety by the addition of alkynylzinc reagent 20 to the aldehyde 19. Furthermore, a new diol protecting group, p-silyloxybenzylidene, was developed for the deprotection from densely functionalized substrates under weakly acidic conditions. The protecting group was easily removed in a two-step procedure ((HF)3.Et3N; AcOH-THF-H2O).

  DOI：

  10.1021/ja0340679
• 作为产物：
  描述：

  [(4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-[1,3]dioxan-4-yl]methyl acetate 在 吡啶 、 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 三氟甲磺酸二丁硼 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 四丁基氢氧化铵 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 44.43h， 生成 ethyl (2Z,4S,5S,6E)-7-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(tritylioxy)ethyl]-[1,3]dioxolan-4-yl}-4-ethyl-5-hydroxyhepta-2,6-dienoate
  参考文献：
  名称：

  Total Synthesis of Leustroducsin B

  摘要：

  A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrization of meso-diol 4 (90.2% ee) and preparation of the C9-C11 anti-diol moiety by the addition of alkynylzinc reagent 20 to the aldehyde 19. Furthermore, a new diol protecting group, p-silyloxybenzylidene, was developed for the deprotection from densely functionalized substrates under weakly acidic conditions. The protecting group was easily removed in a two-step procedure ((HF)3.Et3N; AcOH-THF-H2O).

  DOI：

  10.1021/ja0340679

文献信息

• Total Synthesis of Leustroducsin B
  作者：Kousei Shimada、Yosuke Kaburagi、Tohru Fukuyama

  DOI：10.1021/ja0340679

  日期：2003.4.1

  A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrization of meso-diol 4 (90.2% ee) and preparation of the C9-C11 anti-diol moiety by the addition of alkynylzinc reagent 20 to the aldehyde 19. Furthermore, a new diol protecting group, p-silyloxybenzylidene, was developed for the deprotection from densely functionalized substrates under weakly acidic conditions. The protecting group was easily removed in a two-step procedure ((HF)3.Et3N; AcOH-THF-H2O).