(6R,10S,11R,E)-13,13-diethyl-11-((2S,3S)-3-((4-methoxybenzyl)oxy)-2-methylbutyl)-5-((S)-4-((4-methoxybenzyl)oxy)-2-methylenehept-6-en-1-yl)-2,2,3,3,6,10-hexamethyl-6-((triethylsilyl)oxy)-4,12-dioxa-3,13-disilapentadec-7-ene | 1234064-57-3

• 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: (6R,10S,11R,E)-13,13-diethyl-11-((2S,3S)-3-((4-methoxybenzyl)oxy)-2-methylbutyl)-5-((S)-4-((4-methoxybenzyl)oxy)-2-methylenehept-6-en-1-yl)-2,2,3,3,6,10-hexamethyl-6-((triethylsilyl)oxy)-4,12-dioxa-3,13-disilapentadec-7-ene
• CAS: 1234064-57-3
• 化学式: C₅₆H₉₈O₇Si₃
• 分子量: 967.646
• InChiKey: MQPNGRINMQCYKD-JQWDDBDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.28
• 重原子数：
  66.0
• 可旋转键数：
  34.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (6R,10S,11R,E)-13,13-diethyl-11-((2S,3S)-3-((4-methoxybenzyl)oxy)-2-methylbutyl)-5-((S)-4-((4-methoxybenzyl)oxy)-2-methylenehept-6-en-1-yl)-2,2,3,3,6,10-hexamethyl-6-((triethylsilyl)oxy)-4,12-dioxa-3,13-disilapentadec-7-ene 在 吡啶 、 pyridine hydrofluoride 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以86%的产率得到(2S,3S,5R,6S,10R,15S,E)-11-((tert-butyldimethylsilyl)oxy)-2,15-bis((4-methoxybenzyl)oxy)-3,6,10-trimethyl-13-methylene-10-((triethylsilyl)oxy)octadeca-8,17-dien-5-ol
  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：

  2-[(2S)-2-p-methoxybenzyloxy-4-pentenyl]-1,3-dithiane 在 2,6-二甲基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 cerium(III) chloride 、 2-甲基-2-丁烯 、 水 、 叔丁基锂 、 四氯化锡 、 碳酸氢钠 、 potassium carbonate 、 8-甲氧基-9-硼杂双环[3.3.1]壬烷 、 碘甲烷 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 、 正戊烷 为溶剂， 反应 26.33h， 生成 (6R,10S,11R,E)-13,13-diethyl-11-((2S,3S)-3-((4-methoxybenzyl)oxy)-2-methylbutyl)-5-((S)-4-((4-methoxybenzyl)oxy)-2-methylenehept-6-en-1-yl)-2,2,3,3,6,10-hexamethyl-6-((triethylsilyl)oxy)-4,12-dioxa-3,13-disilapentadec-7-ene
  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