(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-10-(tert-Butyl-diphenyl-silanyloxy)-2,11-bis-(2-hydroxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-3-ol | 205865-30-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: (2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-10-(tert-Butyl-diphenyl-silanyloxy)-2,11-bis-(2-hydroxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-3-ol
• CAS: 205865-30-1
• 化学式: C₃₇H₅₆O₇Si
• 分子量: 640.933
• InChiKey: SJQKIGGRKJSXHI-XRVPPSRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.58
• 重原子数：
  45.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  97.61
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-10-(tert-Butyl-diphenyl-silanyloxy)-2,11-bis-(2-hydroxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-3-ol 在 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 2-[(1R,3S,9R,10S,12S,14R,16R,18S,19R,21S)-18-[tert-butyl(diphenyl)silyl]oxy-10,14,16-trimethylspiro[2,6,8,13,20-pentaoxatetracyclo[10.10.0.03,9.014,21]docosane-7,1'-cyclohexane]-19-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 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以97%的产率得到(2S,3R,4S,5aS,6aR,8R,10S,11R,12aS,13aR)-10-(tert-Butyl-diphenyl-silanyloxy)-2,11-bis-(2-hydroxy-ethyl)-4,6a,8-trimethyl-tetradecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cycloocten-3-ol
  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