(all-S)-phenyl-<3-benzyloxy-3-<5'-(5''-tert-butyldiphenylsiloxymethyltetrahydrofuran-2''-yl)-tetrahydrofuran-2'-yl>propyl>sulfone | 157732-28-0

• 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: (all-S)-phenyl-<3-benzyloxy-3-<5'-(5''-tert-butyldiphenylsiloxymethyltetrahydrofuran-2''-yl)-tetrahydrofuran-2'-yl>propyl>sulfone
• 英文别名: [(2S,5S)-5-[(2S,5S)-5-[(1S)-3-(benzenesulfonyl)-1-phenylmethoxypropyl]oxolan-2-yl]oxolan-2-yl]methoxy-tert-butyl-diphenylsilane
• CAS: 157732-28-0
• 化学式: C₄₁H₅₀O₆SSi
• 分子量: 698.996
• InChiKey: IGVBFWUKPDZPIG-FUVHMUAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.11
• 重原子数：
  49
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (all-S)-phenyl-<3-benzyloxy-3-<5'-(5''-tert-butyldiphenylsiloxymethyltetrahydrofuran-2''-yl)-tetrahydrofuran-2'-yl>propyl>sulfone 在 草酰氯 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 (S)-2-Benzenesulfonyl-4-benzyloxy-1,4-bis-[(2S,5S,2'S,5'S)-5'-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-[2,2']bifuranyl-5-yl]-butan-1-one
  参考文献：
  名称：

  Bidirectional and Convergent Routes to oligo(Tetrahydrofurans)

  摘要：

  AbstractOligo(tetrahydrofurans) (oligo‐THFs) 8–12 have been synthesised stereoselectively. Multiple Williamson reactions were used as key steps. While oligo‐THFs with an even number of THF rings like the bi‐THFs 8 and 9 as well as the tetra‐THFs 10 and 11 were obtained by a bidirectional strategy, the penta‐THF 12 with an odd number of THF rings was prepared by a convergent strategy with a sulfone–aldehyde coupling as connecting step. The oligo‐THF products are important structural features of natural (Annonaceae acetogenins) and non‐natural (artificial ion channels) products.

  DOI：

  10.1002/chem.19970030723
• 作为产物：
  描述：

  (S)-3-Benzyloxy-3-[(2S,5S,2'S,5'S)-5'-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-[2,2']bifuranyl-5-yl]-propan-1-ol 在 吡啶 、 三丁基膦 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (all-S)-phenyl-<3-benzyloxy-3-<5'-(5''-tert-butyldiphenylsiloxymethyltetrahydrofuran-2''-yl)-tetrahydrofuran-2'-yl>propyl>sulfone
  参考文献：
  名称：

  Bidirectional and Convergent Routes to oligo(Tetrahydrofurans)

  摘要：

  AbstractOligo(tetrahydrofurans) (oligo‐THFs) 8–12 have been synthesised stereoselectively. Multiple Williamson reactions were used as key steps. While oligo‐THFs with an even number of THF rings like the bi‐THFs 8 and 9 as well as the tetra‐THFs 10 and 11 were obtained by a bidirectional strategy, the penta‐THF 12 with an odd number of THF rings was prepared by a convergent strategy with a sulfone–aldehyde coupling as connecting step. The oligo‐THF products are important structural features of natural (Annonaceae acetogenins) and non‐natural (artificial ion channels) products.

  DOI：

  10.1002/chem.19970030723

文献信息

• Koert, Ulrich; Stein, Matthias; Harms, Klaus, Angewandte Chemie, 1994, vol. 106, # 11, p. 1238 - 1240
  作者：Koert, Ulrich、Stein, Matthias、Harms, Klaus

  DOI：——

  日期：——
• Bidirectional and Convergent Routes to oligo(Tetrahydrofurans)
  作者：Ulrich Koert、Matthias Stein、Holger Wagner

  DOI：10.1002/chem.19970030723

  日期：1997.7

  AbstractOligo(tetrahydrofurans) (oligo‐THFs) 8–12 have been synthesised stereoselectively. Multiple Williamson reactions were used as key steps. While oligo‐THFs with an even number of THF rings like the bi‐THFs 8 and 9 as well as the tetra‐THFs 10 and 11 were obtained by a bidirectional strategy, the penta‐THF 12 with an odd number of THF rings was prepared by a convergent strategy with a sulfone–aldehyde coupling as connecting step. The oligo‐THF products are important structural features of natural (Annonaceae acetogenins) and non‐natural (artificial ion channels) products.