(1R,2R)-2-(benzyloxy)-1-[(2S,3R,5S)-3-(benzyloxy)-5-(4-tertbutylbenzyl)tetrahydrofuran-2-yl]pent-4-en-1-ol | 1152091-58-1

• 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: (1R,2R)-2-(benzyloxy)-1-[(2S,3R,5S)-3-(benzyloxy)-5-(4-tertbutylbenzyl)tetrahydrofuran-2-yl]pent-4-en-1-ol
• CAS: 1152091-58-1
• 化学式: C₃₄H₄₂O₄
• 分子量: 514.705
• InChiKey: LWCNASDGRXPNIV-PBIPPMFTSA-N

物化性质

• 沸点：
  635.4±55.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  38.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-溴吡啶 、 (1R,2R)-2-(benzyloxy)-1-[(2S,3R,5S)-3-(benzyloxy)-5-(4-tertbutylbenzyl)tetrahydrofuran-2-yl]pent-4-en-1-ol 在 tris-(dibenzylideneacetone)dipalladium(0) 、 双(2-二苯基磷苯基)醚 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 以57%的产率得到(2R,2'R,3R,3'R,5S,5'S)-3-[3,3'-bis(benzyloxy)-5'-(4-tert-butylbenzyl)octahydro-2,2'-bifuran-5-ylmethyl]pyridine
  参考文献：
  名称：

  Synthesis of Fused-Ring and Attached-Ring bis-Tetrahydrofurans via Pd-Catalyzed Carboetherification

  摘要：

  A five step-synthesis of fused bis-tetrahydrofurans and attached bis-tetrahydrofurans from butadiene diepoxide is described. Two sequential Pd-catalyzed carboetherification reactions between protected 1,2-diols and aryl/alkenyl bromides, each of which form both a C-O bond and a C-C bond, are used to generate the heterocyclic rings with >20:1 dr. Installation of different R-1 and R-2 groups is achieved in a straightforward fashion through use of different aryl or alkenyl bromide coupling partners.

  DOI：

  10.1021/ol900594h
• 作为产物：
  描述：

  (1R,2R)-2-(benzyloxy)-1-[(2R,3R,5S)-3-(benzyloxy)-5-(4-tertbutylbenzyl)tetrahydrofuran-2-yl]pent-4-enyloxy(tert-butyl)dimethylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到(1R,2R)-2-(benzyloxy)-1-[(2S,3R,5S)-3-(benzyloxy)-5-(4-tertbutylbenzyl)tetrahydrofuran-2-yl]pent-4-en-1-ol
  参考文献：
  名称：

  Synthesis of Fused-Ring and Attached-Ring bis-Tetrahydrofurans via Pd-Catalyzed Carboetherification

  摘要：

  A five step-synthesis of fused bis-tetrahydrofurans and attached bis-tetrahydrofurans from butadiene diepoxide is described. Two sequential Pd-catalyzed carboetherification reactions between protected 1,2-diols and aryl/alkenyl bromides, each of which form both a C-O bond and a C-C bond, are used to generate the heterocyclic rings with >20:1 dr. Installation of different R-1 and R-2 groups is achieved in a straightforward fashion through use of different aryl or alkenyl bromide coupling partners.

  DOI：

  10.1021/ol900594h