(Z)-6-{(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-10-(tert-Butyl-diphenyl-silanyloxy)-11-[2-(2,2-dimethyl-propionyloxy)-ethyl]-3-hydroxy-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-2-yl}-hex-4-enoic acid | 205865-06-1

• 英文名称: (Z)-6-{(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-10-(tert-Butyl-diphenyl-silanyloxy)-11-[2-(2,2-dimethyl-propionyloxy)-ethyl]-3-hydroxy-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-2-yl}-hex-4-enoic acid
• 英文别名: (Z)-6-[(1R,3S,5S,6R,7S,9R,11S,13R,14S,16R)-14-[tert-butyl(diphenyl)silyl]oxy-13-[2-(2,2-dimethylpropanoyloxy)ethyl]-6-hydroxy-1,5,16-trimethyl-2,8,12-trioxatricyclo[9.6.0.03,9]heptadecan-7-yl]hex-4-enoic acid
• CAS: 205865-06-1
• 化学式: C₄₆H₆₈O₉Si
• 分子量: 793.126
• InChiKey: XHJZKZPYTUCDMO-PQPMZUTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.61
• 重原子数：
  56
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (Z)-6-{(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-10-(tert-Butyl-diphenyl-silanyloxy)-11-[2-(2,2-dimethyl-propionyloxy)-ethyl]-3-hydroxy-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-2-yl}-hex-4-enoic acid 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.0h， 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：

  2,2-Dimethyl-propionic acid 2-[(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-10-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-2-(2-hydroxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-11-yl]-ethyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 水 、 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 为溶剂， 反应 44.5h， 生成 (Z)-6-{(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-10-(tert-Butyl-diphenyl-silanyloxy)-11-[2-(2,2-dimethyl-propionyloxy)-ethyl]-3-hydroxy-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-2-yl}-hex-4-enoic acid
  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