(2S,4R,6S)-2-(4-benzenesulfonyloxyphenyl)-6-[2-(4-benzenesulfonyloxyphenyl)ethyl]-4-{4-methoxy-2,6-bis-[2-(trimethylsilyl)ethoxymethoxy]phenyl}-tetrahydropyran | 886204-71-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: (2S,4R,6S)-2-(4-benzenesulfonyloxyphenyl)-6-[2-(4-benzenesulfonyloxyphenyl)ethyl]-4-{4-methoxy-2,6-bis-[2-(trimethylsilyl)ethoxymethoxy]phenyl}-tetrahydropyran
• 英文别名: [4-[2-[(2S,4R,6S)-6-[4-(benzenesulfonyloxy)phenyl]-4-[4-methoxy-2,6-bis(2-trimethylsilylethoxymethoxy)phenyl]oxan-2-yl]ethyl]phenyl] benzenesulfonate
• CAS: 886204-71-3
• 化学式: C₅₀H₆₄O₁₂S₂Si₂
• 分子量: 977.354
• InChiKey: MCCTUOPBJCLDOD-MSHBZMRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.25
• 重原子数：
  66
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2S,4R,6S)-2-(4-benzenesulfonyloxyphenyl)-6-[2-(4-benzenesulfonyloxyphenyl)ethyl]-4-{4-methoxy-2,6-bis-[2-(trimethylsilyl)ethoxymethoxy]phenyl}-tetrahydropyran 在 N-溴代丁二酰亚胺(NBS) 、 碳酸氢钠 、 potassium carbonate 、 氟化氢吡啶 、 苯基锂 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 23.63h， 生成 epi-calyxin F
  参考文献：
  名称：

  Synthesis and Structure Revision of Calyxin Natural Products

  摘要：

  Tandem Prins cyclization and Friedel-Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations.

  DOI：

  10.1021/jo060094g
• 作为产物：
  描述：

  对羟基苯丙酸 在 4-二甲氨基吡啶 、 氢氧化钾 、 18-冠醚-6 、 三氟化硼乙醚 、 potassium hydride 、 镍 、 二异丁基氢化铝 、 potassium carbonate 、 苯硫酚 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， -78.0~20.0 ℃ 、413.68 kPa 条件下， 反应 52.0h， 生成 (2S,4R,6S)-2-(4-benzenesulfonyloxyphenyl)-6-[2-(4-benzenesulfonyloxyphenyl)ethyl]-4-{4-methoxy-2,6-bis-[2-(trimethylsilyl)ethoxymethoxy]phenyl}-tetrahydropyran
  参考文献：
  名称：

  Synthesis and Structure Revision of Calyxin Natural Products

  摘要：

  Tandem Prins cyclization and Friedel-Crafts reaction with an electron-rich aromatic ring were used to prepare the core structures of calyxin natural products. The proposed structure of epicalyxin F was prepared and shown to be incorrect. Several calyxin natural products, including calyxin F and L, were synthesized, and the structures were reassigned on the basis of NMR data and synthetic correlations.

  DOI：

  10.1021/jo060094g

文献信息

• Catalytic asymmetric hetero-Diels–Alder route to a key intermediate for the synthesis of calyxin L
  作者：Takuya Washio、Hisanori Nambu、Masahiro Anada、Shunichi Hashimoto

  DOI：10.1016/j.tetasy.2007.10.025

  日期：2007.10

  A catalytic asymmetric formal synthesis of diarylheptanoid natural product calyxin L has been achieved by incorporating an enantio- and diastereoselective hetero-Diels-Alder (HDA) reaction, a Suzuki-Miyaura coupling, and a stereocontrolled catalytic hydrogenation of 2,4,6-trisubstituted dihydropyran as the key steps. The HDA reaction between 4-(4-benzyloxyphenyl)-2-triethylsilyloxy-1,3-butadiene and (4-benzenesulfonyloxyphenyl)propynal catalyzed by dirhodium(II) tetrakis[(R)-3-(benzene-fused-phthalimido)-2-piperidinonate], Rh-2(R-BPTPI)(4), provided cis-2,6-disubstituted tetrahydropyran-4-one in 91% yield with 91% ee. (c) 2007 Elsevier Ltd. All rights reserved.