(Z)-6-{(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-3-Acetoxy-10-(tert-butyl-diphenyl-silanyloxy)-11-[2-(2,2-dimethyl-propionyloxy)-ethyl]-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-2-yl}-hex-4-enoic acid methyl ester | 205865-36-7

• 英文名称: (Z)-6-{(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-3-Acetoxy-10-(tert-butyl-diphenyl-silanyloxy)-11-[2-(2,2-dimethyl-propionyloxy)-ethyl]-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-2-yl}-hex-4-enoic acid methyl ester
• CAS: 205865-36-7
• 化学式: C₄₉H₇₂O₁₀Si
• 分子量: 849.19
• InChiKey: QAINAJYOMFEFHC-NISXZTDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.27
• 重原子数：
  60.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  115.82
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (Z)-6-{(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-3-Acetoxy-10-(tert-butyl-diphenyl-silanyloxy)-11-[2-(2,2-dimethyl-propionyloxy)-ethyl]-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-2-yl}-hex-4-enoic acid methyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide 、 水 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 7.0h， 生成 2-[(1R,3S,5Z,11R,12S,14S,16R,18R,20S,21R,23S)-20-[tert-butyl(diphenyl)silyl]oxy-12,16,18-trimethyl-9-oxo-2,10,15,22-tetraoxatetracyclo[12.10.0.03,11.016,23]tetracos-5-en-21-yl]ethyl 2,2-dimethylpropanoate
  参考文献：
  名称：

  Total Synthesis of Brevetoxin A: Part 3: Construction of GHIJ and BCDE Ring Systems

  摘要：

  Successful syntheses of highly complex intermediates 2 (GHIJ ring system) and 3 (BCDE ring system) for the total synthesis of brevetoxin A (1) are described. Several of our methodologies were utilized to achieve this goal: i) hydroxy epoxide cyclizations of intermediates 22 and 30 (rings I and H, respectively); ii) hydroxy dithioketal cyclization of 45 (ring G); and, iii) palladium-catalyzed coupling with bis(cyclic ketene acetal phosphate) 68 (rings B and D). With the knowledge gained from our previous model studies, 2 and 3 were expected to be pivotal intermediates on the synthetic route to brevetoxin A.

  DOI：

  10.1002/(sici)1521-3765(19990201)5:2<628::aid-chem628>3.0.co;2-e
• 作为产物：
  描述：

  (2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-2,11-Bis-(2-benzyloxy-ethyl)-10-(tert-butyl-diphenyl-silanyloxy)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-3-ol 在 palladium on activated charcoal 4-二甲氨基吡啶 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 camphor-10-sulfonic acid 、 氢气 、 4-甲基苯磺酸吡啶 、 双(三甲基硅烷基)氨基钾 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 80.5h， 生成 (Z)-6-{(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-3-Acetoxy-10-(tert-butyl-diphenyl-silanyloxy)-11-[2-(2,2-dimethyl-propionyloxy)-ethyl]-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-2-yl}-hex-4-enoic acid methyl ester
  参考文献：
  名称：

  Total Synthesis of Brevetoxin A: Part 3: Construction of GHIJ and BCDE Ring Systems

  摘要：

  Successful syntheses of highly complex intermediates 2 (GHIJ ring system) and 3 (BCDE ring system) for the total synthesis of brevetoxin A (1) are described. Several of our methodologies were utilized to achieve this goal: i) hydroxy epoxide cyclizations of intermediates 22 and 30 (rings I and H, respectively); ii) hydroxy dithioketal cyclization of 45 (ring G); and, iii) palladium-catalyzed coupling with bis(cyclic ketene acetal phosphate) 68 (rings B and D). With the knowledge gained from our previous model studies, 2 and 3 were expected to be pivotal intermediates on the synthetic route to brevetoxin A.

  DOI：

  10.1002/(sici)1521-3765(19990201)5:2<628::aid-chem628>3.0.co;2-e