(2R,3R,5S,6S)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-6-(4-methoxybenzyloxy)-2,5-dimethylheptanoate | 1192350-63-2

• 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: (2R,3R,5S,6S)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-6-(4-methoxybenzyloxy)-2,5-dimethylheptanoate
• 英文别名: [(1R,2S)-2-[benzyl-(2,4,6-trimethylphenyl)sulfonylamino]-1-phenylpropyl] (2R,3R,5S,6S)-3-hydroxy-6-[(4-methoxyphenyl)methoxy]-2,5-dimethylheptanoate
• CAS: 1192350-63-2
• 化学式: C₄₂H₅₃NO₇S
• 分子量: 715.951
• InChiKey: WCRQVWKKIJAYTD-POUOBEITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  51
• 可旋转键数：
  18
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2R,3R,5S,6S)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-6-(4-methoxybenzyloxy)-2,5-dimethylheptanoate 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 叔丁基锂 、 二异丁基氢化铝 、 三乙胺 、 8-甲氧基-9-硼杂双环[3.3.1]壬烷 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 丙酮 、 甲苯 、 正戊烷 为溶剂， 反应 47.58h， 生成 (5S,10R,14S,15R,E)-5-allyl-3,3,17,17-tetraethyl-15-((2S,3S)-3-(4-methoxybenzyloxy)-2-methylbutyl)-10,14-dimethyl-7-methylene-10-(triethylsilyloxy)-4,16-dioxa-3,17-disilanonadec-11-en-9-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
• 作为产物：
  描述：

  (2R,4S,5R)-5-allyl-2-(4-methoxyphenyl)-4-methyl-1,3-dioxane 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 二异丁基氢化铝 、 臭氧 、 三乙胺 、 双环己基(三氟甲烷磺酰氧基)硼烷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 10.0h， 生成 (2R,3R,5S,6S)-((1R,2S)-2-(N-benzyl-2,4,6-trimethylphenylsulfonamido)-1-phenylpropyl) 3-hydroxy-6-(4-methoxybenzyloxy)-2,5-dimethylheptanoate
  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.