(1S,2R,3S)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)but-3-enyl]-tetrahydrofuran-2-yl}-3-methyl-1-triethylsilanyloxy-hex-5-yn-2-ol | 945265-80-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3S)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)but-3-enyl]-tetrahydrofuran-2-yl}-3-methyl-1-triethylsilanyloxy-hex-5-yn-2-ol
• CAS: 945265-80-5
• 化学式: C₂₈H₄₈O₅Si
• 分子量: 492.772
• InChiKey: YYTBIRPVVRFVFW-LTIOPVOZSA-N

物化性质

• 沸点：
  547.6±50.0 °C(predicted)
• 密度：
  1.027±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  34.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)but-3-enyl]-tetrahydrofuran-2-yl}-3-methyl-1-triethylsilanyloxy-hex-5-yn-2-ol 在 Grubbs catalyst first generation Bu3SnAlEt2 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 生成 (1S,2R,3R,6R,7E,9E,11R,12R,13E,17S)-2,11,12-trihydroxy-3-((S)-4-iodopent-4-en-2-yl)-6-methyl-4,20-dioxabicyclo[15.2.1]icosa-7,9,13-trien-5-one
  参考文献：
  名称：

  Total synthesis of amphidinolide E and amphidinolide E stereoisomers

  摘要：

  Four amphidinolide E stereoisomers, amphidinolide E (1), 2-epi-amphidinolide E (2), 19-epi-amphidinolide E (3), and 2-epi-19-epi- amphidinolide E (4), have been synthesized via the judicious union of aldehyde 5, allylsilanes 7 or 8, acids 9 or 10, and vinylstannane 6. The C19 stereocenters of the C19 epimeric allylsilanes 7 and 8 were introduced via crotylboration reactions early in the synthesis. [3+2] Annulation reactions of aldehyde 5 with allylsilanes 7 and 8 were employed to set the core tetrahydrofuran units of 1-4. Finally, the C2 stereo-center was installed by esterification using acid 9, without incident, or with acid 10, in which case an unexpected and completely stereoselective inversion of C2 occurs. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.058
• 作为产物：
  描述：

  在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 以0.34 g的产率得到(1S,2R,3S)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)but-3-enyl]-tetrahydrofuran-2-yl}-3-methyl-1-triethylsilanyloxy-hex-5-yn-2-ol
  参考文献：
  名称：

  Total synthesis of amphidinolide E and amphidinolide E stereoisomers

  摘要：

  Four amphidinolide E stereoisomers, amphidinolide E (1), 2-epi-amphidinolide E (2), 19-epi-amphidinolide E (3), and 2-epi-19-epi- amphidinolide E (4), have been synthesized via the judicious union of aldehyde 5, allylsilanes 7 or 8, acids 9 or 10, and vinylstannane 6. The C19 stereocenters of the C19 epimeric allylsilanes 7 and 8 were introduced via crotylboration reactions early in the synthesis. [3+2] Annulation reactions of aldehyde 5 with allylsilanes 7 and 8 were employed to set the core tetrahydrofuran units of 1-4. Finally, the C2 stereo-center was installed by esterification using acid 9, without incident, or with acid 10, in which case an unexpected and completely stereoselective inversion of C2 occurs. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.058