(1S,2R,3R,4R,8R,9R,11R)-3-[tert-butyl(dimethyl)silyl]oxy-11-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,6,6-trimethyl-5,7,15-trioxatetracyclo[9.3.1.01,9.04,8]pentadec-12-en-14-one | 916599-81-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (1S,2R,3R,4R,8R,9R,11R)-3-[tert-butyl(dimethyl)silyl]oxy-11-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,6,6-trimethyl-5,7,15-trioxatetracyclo[9.3.1.01,9.04,8]pentadec-12-en-14-one
• CAS: 916599-81-0
• 化学式: C₂₈H₅₀O₆Si₂
• 分子量: 538.872
• InChiKey: ZVCFIMZJWZSYBQ-ZKVOLBIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.22
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (1S,2R,3R,4R,8R,9R,11R)-3-[tert-butyl(dimethyl)silyl]oxy-11-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,6,6-trimethyl-5,7,15-trioxatetracyclo[9.3.1.01,9.04,8]pentadec-12-en-14-one 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 反应 0.33h， 以89%的产率得到
  参考文献：
  名称：

  Studies on Oxidopyrylium [5 + 2] Cycloadditions:  Toward a General Synthetic Route to the C12-Hydroxy Daphnetoxins

  摘要：

  [GRAPHICS]12-Hydroxydaphnetoxins, members of the structurally fascinating daphnane diterpene family, exhibit a wide range of significant biological activities. A general route to the BC-ring system of 12-hydroxy daphnetoxins is reported based on D-ribose. Depending on the choice of protecting groups and solvent, the oxidopyrylium-alkene [5+2] cycloaddition originating from A provides cycloadduct diastereomer B or C with good to excellent selectivity.

  DOI：

  10.1021/ol062234e
• 作为产物：
  描述：

  (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 在 吡啶 、 2,6-二甲基吡啶 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 四丙基高钌酸铵 、 bis(acetylacetonate)oxovanadium 、 4 A molecular sieve 、 氯代二环己基硼烷 、 二异丁基氢化铝 、 溶剂黄146 、 N-甲基吗啉氧化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 柠檬酸 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 31.59h， 生成 (1S,2R,3R,4R,8R,9R,11R)-3-[tert-butyl(dimethyl)silyl]oxy-11-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,6,6-trimethyl-5,7,15-trioxatetracyclo[9.3.1.01,9.04,8]pentadec-12-en-14-one
  参考文献：
  名称：

  Studies on Oxidopyrylium [5 + 2] Cycloadditions:  Toward a General Synthetic Route to the C12-Hydroxy Daphnetoxins

  摘要：

  [GRAPHICS]12-Hydroxydaphnetoxins, members of the structurally fascinating daphnane diterpene family, exhibit a wide range of significant biological activities. A general route to the BC-ring system of 12-hydroxy daphnetoxins is reported based on D-ribose. Depending on the choice of protecting groups and solvent, the oxidopyrylium-alkene [5+2] cycloaddition originating from A provides cycloadduct diastereomer B or C with good to excellent selectivity.

  DOI：

  10.1021/ol062234e

文献信息

• Studies on Oxidopyrylium [5 + 2] Cycloadditions:  Toward a General Synthetic Route to the C12-Hydroxy Daphnetoxins
  作者：Paul A. Wender、F. Christopher Bi、Nicole Buschmann、Francis Gosselin、Cindy Kan、Jung-Min Kee、Hirofumi Ohmura

  DOI：10.1021/ol062234e

  日期：2006.11.9

  [GRAPHICS]12-Hydroxydaphnetoxins, members of the structurally fascinating daphnane diterpene family, exhibit a wide range of significant biological activities. A general route to the BC-ring system of 12-hydroxy daphnetoxins is reported based on D-ribose. Depending on the choice of protecting groups and solvent, the oxidopyrylium-alkene [5+2] cycloaddition originating from A provides cycloadduct diastereomer B or C with good to excellent selectivity.