methyl (1S,3S,4S,6R,7R,8S)-1-(tert-butyldimethylsiloxy)-6-methyl-10-oxatricyclo[5.2.1.0^4,8]-dec-3-yl-carboxylate | 949585-44-8

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: methyl (1S,3S,4S,6R,7R,8S)-1-(tert-butyldimethylsiloxy)-6-methyl-10-oxatricyclo[5.2.1.0^4,8]-dec-3-yl-carboxylate
• CAS: 949585-44-8
• 化学式: C₁₈H₃₂O₄Si
• 分子量: 340.535
• InChiKey: NFYXPJMRQNXWFB-OFULCDIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl (1S,3S,4S,6R,7R,8S)-1-(tert-butyldimethylsiloxy)-6-methyl-10-oxatricyclo[5.2.1.0^4,8]-dec-3-yl-carboxylate 在 咪唑 、 lithium aluminium tetrahydride 、 丁硫醇 、 四丁基氟化铵 、 仲丁基锂 、 4-甲基苯磺酸吡啶 、 N,N-二异丙基乙胺 、 magnesium bromide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 环己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.5h， 生成 (1R,2S,6S,7R,8R)-2-(hydroxymethyl)-8-methyl-7-(triethylsiloxy)bicyclo[4.3.0]non-3-ene
  参考文献：
  名称：

  Towards EPC-syntheses of the structural class of cochleamycins and macquarimicins. Part 2: EPC-synthesis of the hydrindene subunit of the macquarimicins

  摘要：

  The EPC-synthesis of the cis- hydrindene subunit of the macquarimicins, antibiotics with antitumour and anti-inflammatory activity, has been achieved. Desymmetrization of cis-1,4-cyclopent-2-enediol was succeeded by Diels-Alder reaction and functional group transformations to a tricyclic ketone. Regio- and stereoselective methylation via Claisen condensation and hydrogenation was followed by nucleophilic, intramolecular addition, reduction and acidic fragmentation. Further functional group transformations led to the target molecule. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.094
• 作为产物：
  描述：

  叔丁基二甲硅基三氟甲磺酸酯 、 methyl (1S,2S,6S,7R,8R)-7-hydroxy-8-methyl-4-oxobicyclo[4.3.0]non-2-yl-carboxylate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 methyl (1S,3S,4S,6R,7R,8S)-1-(tert-butyldimethylsiloxy)-6-methyl-10-oxatricyclo[5.2.1.0^4,8]-dec-3-yl-carboxylate
  参考文献：
  名称：

  Towards EPC-syntheses of the structural class of cochleamycins and macquarimicins. Part 2: EPC-synthesis of the hydrindene subunit of the macquarimicins

  摘要：

  The EPC-synthesis of the cis- hydrindene subunit of the macquarimicins, antibiotics with antitumour and anti-inflammatory activity, has been achieved. Desymmetrization of cis-1,4-cyclopent-2-enediol was succeeded by Diels-Alder reaction and functional group transformations to a tricyclic ketone. Regio- and stereoselective methylation via Claisen condensation and hydrogenation was followed by nucleophilic, intramolecular addition, reduction and acidic fragmentation. Further functional group transformations led to the target molecule. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.094