(S)-3-Benzyloxy-3-[(2S,5S,2'S,5'S)-5'-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-[2,2']bifuranyl-5-yl]-propionaldehyde | 195731-40-9

• 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: (S)-3-Benzyloxy-3-[(2S,5S,2'S,5'S)-5'-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-[2,2']bifuranyl-5-yl]-propionaldehyde
• CAS: 195731-40-9
• 化学式: C₃₅H₄₄O₅Si
• 分子量: 572.817
• InChiKey: SPYVMLPGVAWMMB-KMACTHOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.83
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S)-3-Benzyloxy-3-[(2S,5S,2'S,5'S)-5'-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-[2,2']bifuranyl-5-yl]-propionaldehyde 在 palladium on activated charcoal 吡啶 、 丙醇 、 sodium tetrahydroborate 、 aluminum amalgam 、 草酰氯 、 三丁基膦 、 氢气 、 sodium hydride 、 magnesium monoperoxyphthalate hexahydrate 、 二甲基亚砜 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 25.0h， 生成 (2S,5S,2'S,5'S,2''S,5''R,2'''S,5'''S,2''''S,5''''S)-5,5''''-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-icosahydro-[2,2';5',2'';5'',2''';5''',2'''']quinquefuran
  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：

  (all-S)-<5-(5'-tert-butyldiphenylsiloxymethyltetrahydrofuran-2'-yl)-2-(1''-benzyloxy-3''-buten-1''-yl)>-tetrahydrofuran 在 臭氧 、 三苯基膦 作用下， 生成 (S)-3-Benzyloxy-3-[(2S,5S,2'S,5'S)-5'-(tert-butyl-diphenyl-silanyloxymethyl)-octahydro-[2,2']bifuranyl-5-yl]-propionaldehyde
  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