(3R,4R,6S)-1-[tert-butyl(diphenyl)silyl]oxy-7-[(4-methoxyphenyl)methoxy]-3,6-dimethylheptane-3,4-diol | 1549648-57-8

• 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: (3R,4R,6S)-1-[tert-butyl(diphenyl)silyl]oxy-7-[(4-methoxyphenyl)methoxy]-3,6-dimethylheptane-3,4-diol
• CAS: 1549648-57-8
• 化学式: C₃₃H₄₆O₅Si
• 分子量: 550.811
• InChiKey: QTGGENPBVUPTRO-MBHRIBFBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.32
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R,6S)-1-[tert-butyl(diphenyl)silyl]oxy-7-[(4-methoxyphenyl)methoxy]-3,6-dimethylheptane-3,4-diol 在 2,6-二甲基吡啶 、 aluminum tri-bromide 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 (4S,5S)-chloro(cyclopentadienyl)(2,2-dimethyl-α,α,α',α'-tetraphenyl-1,3-dioxolane-4,5-dimethanolato-O,O^α)titanium 、 四丁基氟化铵 、 水 、 对甲苯磺酸 、 溶剂黄146 、 乙氧基乙炔 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 70.67h， 生成 (2S,3R,5R)-5-methyl-2-(3-methylbut-3-enyl)-5-propyltetrahydrofuran-3-yl (2E)-(4S,7R,9S,10R)-9-(tert-butyldimethylsilyloxy)-4,7,10-trimethyl-6-oxo-7-(triethylsilyl)oxydodeca-2,11-dienoate
  参考文献：
  名称：

  Synthesis of amphidinolide Y precursors

  摘要：

  The Negishi coupling between a chiral C3 synthon and an iodoalkene arising from 3-butyn-l-ol, which gave the C3-C9 fragment of amphidinolide Y, was the starting point of a formal total synthesis of this marine natural product. By means of Sharpless ADH and TADDOL-mediated crotylation, the full western fragment (C1-C11) was obtained, which was coupled with the eastern fragment (3-hydroxyoxolane derivative). The penultimate step (ring-closing metathesis, with G-II, H-G-II, or Nitro-Grela reagents, under several conditions) posed great difficulties. The cyclization was achieved with 15c (7,9-bis-O-TES) and 15d (7-O-TES, 9-O-TBS); more than stoichiometric amounts of the H-G-II Ru complex were required for complete conversion. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.047
• 作为产物：
  描述：

  (3-丁炔-1-基氧基)(2-甲基-2-丙基)二苯基硅烷 在 二氯二茂锆 、 甲基磺酰胺 、 AD-mix β 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 81.67h， 生成 (3R,4R,6S)-1-[tert-butyl(diphenyl)silyl]oxy-7-[(4-methoxyphenyl)methoxy]-3,6-dimethylheptane-3,4-diol
  参考文献：
  名称：

  Synthesis of amphidinolide Y precursors

  摘要：

  The Negishi coupling between a chiral C3 synthon and an iodoalkene arising from 3-butyn-l-ol, which gave the C3-C9 fragment of amphidinolide Y, was the starting point of a formal total synthesis of this marine natural product. By means of Sharpless ADH and TADDOL-mediated crotylation, the full western fragment (C1-C11) was obtained, which was coupled with the eastern fragment (3-hydroxyoxolane derivative). The penultimate step (ring-closing metathesis, with G-II, H-G-II, or Nitro-Grela reagents, under several conditions) posed great difficulties. The cyclization was achieved with 15c (7,9-bis-O-TES) and 15d (7-O-TES, 9-O-TBS); more than stoichiometric amounts of the H-G-II Ru complex were required for complete conversion. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.047

文献信息

• Synthesis of amphidinolide Y precursors
  作者：Laura Mola、Anna Olivella、Fèlix Urpí、Jaume Vilarrasa

  DOI：10.1016/j.tetlet.2013.12.047

  日期：2014.1

  The Negishi coupling between a chiral C3 synthon and an iodoalkene arising from 3-butyn-l-ol, which gave the C3-C9 fragment of amphidinolide Y, was the starting point of a formal total synthesis of this marine natural product. By means of Sharpless ADH and TADDOL-mediated crotylation, the full western fragment (C1-C11) was obtained, which was coupled with the eastern fragment (3-hydroxyoxolane derivative). The penultimate step (ring-closing metathesis, with G-II, H-G-II, or Nitro-Grela reagents, under several conditions) posed great difficulties. The cyclization was achieved with 15c (7,9-bis-O-TES) and 15d (7-O-TES, 9-O-TBS); more than stoichiometric amounts of the H-G-II Ru complex were required for complete conversion. (C) 2013 Elsevier Ltd. All rights reserved.