(2R,6S,7R,9S,10S,E)-2-((2S,6S)-6-allyl-2-hydroxy-4-methylenetetrahydro-2H-pyran-2-yl)-10-(4-methoxybenzyloxy)-6,9-dimethylundec-3-ene-2,7-diol | 1192350-56-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2R,6S,7R,9S,10S,E)-2-((2S,6S)-6-allyl-2-hydroxy-4-methylenetetrahydro-2H-pyran-2-yl)-10-(4-methoxybenzyloxy)-6,9-dimethylundec-3-ene-2,7-diol
• 英文别名: (E,2R,6S,7R,9S,10S)-2-[(2S,6S)-2-hydroxy-4-methylidene-6-prop-2-enyloxan-2-yl]-10-[(4-methoxyphenyl)methoxy]-6,9-dimethylundec-3-ene-2,7-diol
• CAS: 1192350-56-3
• 化学式: C₃₀H₄₆O₆
• 分子量: 502.692
• InChiKey: MNEZHOZQAXYFNU-WVFCHYLQSA-N

物化性质

• 沸点：
  629.8±55.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,6S,7R,9S,10S,E)-2-((2S,6S)-6-allyl-2-hydroxy-4-methylenetetrahydro-2H-pyran-2-yl)-10-(4-methoxybenzyloxy)-6,9-dimethylundec-3-ene-2,7-diol 在 2,4,6-三氯苯甲酰氯 、 水 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.5h， 生成
  参考文献：
  名称：

  Total synthesis of the proposed structure of iriomoteolide-1a

  摘要：

  Full details of the total synthesis of the proposed structure of iriomoteolide-1a (1) are described. The key steps include (i) a Sakurai reaction between allylsilane 11 and aldehyde 10 that bears both a tertiary chiral center and vinyl iodide moiety (ii) an anti-aldol reaction to construct the C18/C19 chiral centers (iii) a B-alkyl Suzuki-Miyaura coupling reaction to assemble the C7-C23 fragment, and (iv) a macrocyclic ring-closing metathesis to complete the construction of the target molecule. Two different approaches to access penultimate precursor 2 are delineated. The NMR spectra of the synthetic iriomoteolide-1a (1) were found not to match those reported for the natural product bringing into question its true structural identity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.066
• 作为产物：
  描述：

  (S)-2-allyloxirane 在 吡啶 、 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 pyridine hydrofluoride 、 叔丁基锂 、 三氧化硫吡啶 、 四氯化锡 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 8-甲氧基-9-硼杂双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 正戊烷 为溶剂， 反应 16.08h， 生成 (2R,6S,7R,9S,10S,E)-2-((2S,6S)-6-allyl-2-hydroxy-4-methylenetetrahydro-2H-pyran-2-yl)-10-(4-methoxybenzyloxy)-6,9-dimethylundec-3-ene-2,7-diol
  参考文献：
  名称：

  Total synthesis of the proposed structure of iriomoteolide-1a

  摘要：

  Full details of the total synthesis of the proposed structure of iriomoteolide-1a (1) are described. The key steps include (i) a Sakurai reaction between allylsilane 11 and aldehyde 10 that bears both a tertiary chiral center and vinyl iodide moiety (ii) an anti-aldol reaction to construct the C18/C19 chiral centers (iii) a B-alkyl Suzuki-Miyaura coupling reaction to assemble the C7-C23 fragment, and (iv) a macrocyclic ring-closing metathesis to complete the construction of the target molecule. Two different approaches to access penultimate precursor 2 are delineated. The NMR spectra of the synthetic iriomoteolide-1a (1) were found not to match those reported for the natural product bringing into question its true structural identity. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.066

文献信息

• Asymmetric Synthesis of the C(7)−C(23) Fragment of Iriomoteolide-1a
  作者：Jun Xie、Yuelong Ma、David A Horne

  DOI：10.1021/ol902110a

  日期：2009.11.5

  An efficient synthesis of the C(7)-C(23) fragment 2 of iriomoteolide-1a (1) has been accomplished via a B-alkyl Suzuki-Miyaura cross-coupling reaction followed by deprotection and cyclization to form the cyclic hemiketal core.
• Total synthesis of the proposed structure of iriomoteolide-1a
  作者：Jun Xie、Yuelong Ma、David A. Horne

  DOI：10.1016/j.tet.2011.07.066

  日期：2011.9

  Full details of the total synthesis of the proposed structure of iriomoteolide-1a (1) are described. The key steps include (i) a Sakurai reaction between allylsilane 11 and aldehyde 10 that bears both a tertiary chiral center and vinyl iodide moiety (ii) an anti-aldol reaction to construct the C18/C19 chiral centers (iii) a B-alkyl Suzuki-Miyaura coupling reaction to assemble the C7-C23 fragment, and (iv) a macrocyclic ring-closing metathesis to complete the construction of the target molecule. Two different approaches to access penultimate precursor 2 are delineated. The NMR spectra of the synthetic iriomoteolide-1a (1) were found not to match those reported for the natural product bringing into question its true structural identity. (C) 2011 Elsevier Ltd. All rights reserved.