(1E,3S,4R)-3,4-epoxy-2,3-dimethyl-1-triisopropylsilyl-5-triisopropylsilyloxy-1-pentene | 1330680-55-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1E,3S,4R)-3,4-epoxy-2,3-dimethyl-1-triisopropylsilyl-5-triisopropylsilyloxy-1-pentene
• CAS: 1330680-55-1
• 化学式: C₂₅H₅₂O₂Si₂
• 分子量: 440.858
• InChiKey: MKFFAISYVFXUAA-VBVNTZJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.5
• 重原子数：
  29.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  21.76
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1E,3S,4R)-3,4-epoxy-2,3-dimethyl-1-triisopropylsilyl-5-triisopropylsilyloxy-1-pentene 在 N-碘代丁二酰亚胺 作用下， 以 六氟异丙醇 为溶剂， 以90%的产率得到(1E,3S,4R)-3,4-epoxy-1-iodo-2,3-dimethyl-5-trisopropylsyliloxy-4-pentene
  参考文献：
  名称：

  Iododesilylation of TIPS-, TBDPS-, and TBS-Substituted Alkenes in Connection with the Synthesis of Amphidinolides B/D

  摘要：

  The C-Si bonds of triisopropylsilyl-substituted alkenes, 1,3-dienes, and related multifunctional substrates, as well as analogous C-TBDPS and C-TBS bonds, are readily and chemoselectively cleaved with NIS (or other sources of I(+), such as N-iodosaccharin, 1,3-diodohydantoin, and Ipy(2)BF(4)). The desired iodoalkenes are obtained stereospecifically without byproducts, provided that the reactions are carried out in CF(3)CHOHCF(3) and, in general, with 30 mol % of Ag(2)CO(3) (or AgOAc/2,6-Iutidine) as an additive. Fragment C10-C18 of cytotoxic amphidinolides B1-B3 and D has been synthesized using this improved procedure.

  DOI：

  10.1021/ol2020187
• 作为产物：
  描述：

  在 咪唑 、 titanium(IV) isopropylate 、 四(三苯基膦)钯 、 二叔丁基过氧化物 、 D-(-)-酒石酸二异丙酯 、 sodium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 (1E,3S,4R)-3,4-epoxy-2,3-dimethyl-1-triisopropylsilyl-5-triisopropylsilyloxy-1-pentene
  参考文献：
  名称：

  Iododesilylation of TIPS-, TBDPS-, and TBS-Substituted Alkenes in Connection with the Synthesis of Amphidinolides B/D

  摘要：

  The C-Si bonds of triisopropylsilyl-substituted alkenes, 1,3-dienes, and related multifunctional substrates, as well as analogous C-TBDPS and C-TBS bonds, are readily and chemoselectively cleaved with NIS (or other sources of I(+), such as N-iodosaccharin, 1,3-diodohydantoin, and Ipy(2)BF(4)). The desired iodoalkenes are obtained stereospecifically without byproducts, provided that the reactions are carried out in CF(3)CHOHCF(3) and, in general, with 30 mol % of Ag(2)CO(3) (or AgOAc/2,6-Iutidine) as an additive. Fragment C10-C18 of cytotoxic amphidinolides B1-B3 and D has been synthesized using this improved procedure.

  DOI：

  10.1021/ol2020187