2,2-Dimethyl-propionic acid 2-[(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-3-acetoxy-10-(tert-butyl-diphenyl-silanyloxy)-2-(2-hydroxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-11-yl]-ethyl ester | 205865-05-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-Dimethyl-propionic acid 2-[(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-3-acetoxy-10-(tert-butyl-diphenyl-silanyloxy)-2-(2-hydroxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-11-yl]-ethyl ester
• 英文别名: 2-[(1R,3S,5S,6R,7S,9R,11S,13R,14S,16R)-6-acetyloxy-14-[tert-butyl(diphenyl)silyl]oxy-7-(2-hydroxyethyl)-1,5,16-trimethyl-2,8,12-trioxatricyclo[9.6.0.03,9]heptadecan-13-yl]ethyl 2,2-dimethylpropanoate
• CAS: 205865-05-0
• 化学式: C₄₄H₆₆O₉Si
• 分子量: 767.088
• InChiKey: LINLOJSUYQQFGY-DLXOCWFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.75
• 重原子数：
  54
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-propionic acid 2-[(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-3-acetoxy-10-(tert-butyl-diphenyl-silanyloxy)-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 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 10.0h， 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 、 camphor-10-sulfonic acid 、 氢气 、 4-甲基苯磺酸吡啶 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.5h， 生成 2,2-Dimethyl-propionic acid 2-[(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-3-acetoxy-10-(tert-butyl-diphenyl-silanyloxy)-2-(2-hydroxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-11-yl]-ethyl 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