(3S,5S,6R)-3-triisopropylsilyloxy-5-tert-butyldimethylsilyloxy-6-ethoxycarbonyloxy-hept-1-ene | 1291067-34-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: (3S,5S,6R)-3-triisopropylsilyloxy-5-tert-butyldimethylsilyloxy-6-ethoxycarbonyloxy-hept-1-ene
• CAS: 1291067-34-9
• 化学式: C₂₅H₅₂O₅Si₂
• 分子量: 488.856
• InChiKey: BJPZOBPZWDKJLF-ZLNRFVROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.08
• 重原子数：
  32.0
• 可旋转键数：
  13.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (3S,5S,6R)-3-triisopropylsilyloxy-5-tert-butyldimethylsilyloxy-6-ethoxycarbonyloxy-hept-1-ene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以83%的产率得到(4S,5R)-4-((S)-2-hydroxy-but-3-enyl)-5-methyl-[1,3]dioxolan-2-one
  参考文献：
  名称：

  Synthesis of hept-6-en-2,4,5-triols and hept-6-en-2,3,5-triols

  摘要：

  In a systematic effort to establish the relative as well as absolute configurations of two natural products isolated from Asomycete Daldinia concentrica, four independent (non-antipodal) diastereomers of hept-6-en-2,4,5-triol, the structure previously proposed for the natural products, were synthesized in enantiopure forms through a chiral-pool route and their optical rotation as well as NMR data were recorded. Although these four synthetic isomers cover all possible relative configurations the originally assigned triol may have, none of them gave spectroscopic data compatible with those reported for the natural products. Similar negative results were also obtained with a group of four non-antipodal diastereomers of hept-6-en-2,3,5-triol. The genuine structures of the natural products are therefore to be re-assigned. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.091
• 作为产物：
  描述：

  三异丙基氯硅烷 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 silica-supported sodium periodate 、 水 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 33.0h， 生成 (3S,5S,6R)-3-triisopropylsilyloxy-5-tert-butyldimethylsilyloxy-6-ethoxycarbonyloxy-hept-1-ene
  参考文献：
  名称：

  Synthesis of hept-6-en-2,4,5-triols and hept-6-en-2,3,5-triols

  摘要：

  In a systematic effort to establish the relative as well as absolute configurations of two natural products isolated from Asomycete Daldinia concentrica, four independent (non-antipodal) diastereomers of hept-6-en-2,4,5-triol, the structure previously proposed for the natural products, were synthesized in enantiopure forms through a chiral-pool route and their optical rotation as well as NMR data were recorded. Although these four synthetic isomers cover all possible relative configurations the originally assigned triol may have, none of them gave spectroscopic data compatible with those reported for the natural products. Similar negative results were also obtained with a group of four non-antipodal diastereomers of hept-6-en-2,3,5-triol. The genuine structures of the natural products are therefore to be re-assigned. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.091