(1S,2R,3R,4R,5R,6R,8R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-12-oxa-tricyclo[6.3.1.0^1,6]dodec-9-en-11-one | 916599-87-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,2R,3R,4R,5R,6R,8R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-12-oxa-tricyclo[6.3.1.0^1,6]dodec-9-en-11-one
• 英文别名: (1S,2R,3R,4R,5R,6R,8R)-3-[tert-butyl(dimethyl)silyl]oxy-8-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-methyl-4,5-bis(phenylmethoxy)-12-oxatricyclo[6.3.1.01,6]dodec-9-en-11-one
• CAS: 916599-87-6
• 化学式: C₃₉H₅₈O₆Si₂
• 分子量: 679.057
• InChiKey: BASNVVOLPYMMJZ-JVJREBKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.87
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 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,5R,6R,8R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-12-oxa-tricyclo[6.3.1.0^1,6]dodec-9-en-11-one 在 palladium dihydroxide 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、101.32 kPa 条件下， 以84%的产率得到(1S,2R,3R,4R,5R,6R,8S)-3-(tert-Butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-4,5-dihydroxy-2-methyl-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-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
• 作为产物：
  描述：

  (4S,5R)-4,5-Bis-benzyloxy-hept-6-en-3-ol 在 吡啶 、 2,6-二甲基吡啶 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 锂硼氢 、 四丙基高钌酸铵 、 bis(acetylacetonate)oxovanadium 、 4 A molecular sieve 、 氯代二环己基硼烷 、 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 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 67.66h， 生成 (1S,2R,3R,4R,5R,6R,8R)-4,5-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-dimethyl-silanyloxymethyl)-2-methyl-12-oxa-tricyclo[6.3.1.0^1,6]dodec-9-en-11-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