methyl (Z)-3-[(2R,3R,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-methyl-2,3,4,5,8,9-hexahydrooxonin-9-yl]-2-methoxyprop-2-enoate | 1254294-99-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl (Z)-3-[(2R,3R,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-methyl-2,3,4,5,8,9-hexahydrooxonin-9-yl]-2-methoxyprop-2-enoate
• CAS: 1254294-99-9
• 化学式: C₂₇H₅₂O₆Si₂
• 分子量: 528.877
• InChiKey: LTLXDGASDBZBCL-HYQFCGDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.99
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (Z)-3-[(2R,3R,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-methyl-2,3,4,5,8,9-hexahydrooxonin-9-yl]-2-methoxyprop-2-enoate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure of Briarellin J

  摘要：

  The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.

  DOI：

  10.1021/ol102169w
• 作为产物：
  描述：

  (2R,8R,9R)-8-(tert-butyldimethylsilanyloxy)-9-(tert-butyldimethylsilanyloxymethyl)-4-methyl-2,3,4,5,8,9-hexahydrooxonine-2-carbaldehyde 、 methyl 2-methoxy-2-(triphenylphosphonium)acetate chloride 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 18.5h， 以4.26 g的产率得到methyl (Z)-3-[(2R,3R,6Z,9R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-methyl-2,3,4,5,8,9-hexahydrooxonin-9-yl]-2-methoxyprop-2-enoate
  参考文献：
  名称：

  Total Synthesis of the Proposed Structure of Briarellin J

  摘要：

  The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.

  DOI：

  10.1021/ol102169w

文献信息

• Total Synthesis of the Proposed Structure of Briarellin J
  作者：Michael T. Crimmins、Mark C. Mans、Abimael D. Rodríguez

  DOI：10.1021/ol102169w

  日期：2010.11.5

  The total synthesis of the originally proposed structure of briarellin J is reported in 15 steps from a known compound and in 23 steps from readily available materials. Key reactions include an exo-selective intramolecular Diels-Alder and a substrate-controlled hydroboration. Discrepancies in the spectroscopic data of the synthetic and natural material led to a revision of the assigned structure.