(5R,10S)-10-allyl-3,3,12,12-tetraethyl-5-((E)-2-iodovinyl)-5-methyl-8-methylene-4,11-dioxa-3,12-disilatetradecan-6-yl acetate | 1192350-57-4

• 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: (5R,10S)-10-allyl-3,3,12,12-tetraethyl-5-((E)-2-iodovinyl)-5-methyl-8-methylene-4,11-dioxa-3,12-disilatetradecan-6-yl acetate
• 英文别名: [(1E,3R,8S)-1-iodo-3-methyl-6-methylidene-3,8-bis(triethylsilyloxy)undeca-1,10-dien-4-yl] acetate
• CAS: 1192350-57-4
• 化学式: C₂₇H₅₁IO₄Si₂
• 分子量: 622.775
• InChiKey: YCSBDNIYGPAECF-AZTOMZQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.95
• 重原子数：
  34
• 可旋转键数：
  20
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R,10S)-10-allyl-3,3,12,12-tetraethyl-5-((E)-2-iodovinyl)-5-methyl-8-methylene-4,11-dioxa-3,12-disilatetradecan-6-yl acetate 在 吡啶 、 lithium aluminium tetrahydride 、 pyridine hydrofluoride 、 2,4,6-三氯苯甲酰氯 、 叔丁基锂 、 三氧化硫吡啶 、 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 25.83h， 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：

  (4S)-2-(trimethylsilylmethyl)hepta-1,6-dien-4-ol 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 四氯化锡 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.25h， 生成 (5R,10S)-10-allyl-3,3,12,12-tetraethyl-5-((E)-2-iodovinyl)-5-methyl-8-methylene-4,11-dioxa-3,12-disilatetradecan-6-yl acetate
  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.