(1S,3R,8R,10S,12R,14R,15S,17R,19R)-15-[tert-butyl(dimethyl)silyl]oxy-8-[[tert-butyl(dimethyl)silyl]oxymethyl]-17-[3-[tert-butyl(diphenyl)silyl]oxypropyl]-10-methyl-2,9,13,18-tetraoxatetracyclo[10.8.0.03,10.014,19]icosan-7-one | 221381-16-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,8R,10S,12R,14R,15S,17R,19R)-15-[tert-butyl(dimethyl)silyl]oxy-8-[[tert-butyl(dimethyl)silyl]oxymethyl]-17-[3-[tert-butyl(diphenyl)silyl]oxypropyl]-10-methyl-2,9,13,18-tetraoxatetracyclo[10.8.0.03,10.014,19]icosan-7-one
• CAS: 221381-16-4
• 化学式: C₄₉H₈₀O₈Si₃
• 分子量: 881.426
• InChiKey: UUORQSXIINKCNV-HWPKNYEQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.12
• 重原子数：
  60
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,3R,8R,10S,12R,14R,15S,17R,19R)-15-[tert-butyl(dimethyl)silyl]oxy-8-[[tert-butyl(dimethyl)silyl]oxymethyl]-17-[3-[tert-butyl(diphenyl)silyl]oxypropyl]-10-methyl-2,9,13,18-tetraoxatetracyclo[10.8.0.03,10.014,19]icosan-7-one 在 pyridine-SO3 complex 、 4-甲基苯磺酸吡啶 、 zinc trifluoromethanesulfonate 、 碳酸氢钠 、 二甲基亚砜 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 9.5h， 生成 (1S,3R,8R,10S,12R,14R,15S,17R,19R)-15-[tert-butyl(dimethyl)silyl]oxy-17-[3-[tert-butyl(diphenyl)silyl]oxypropyl]-7,7-bis(ethylsulfanyl)-10-methyl-2,9,13,18-tetraoxatetracyclo[10.8.0.03,10.014,19]icosane-8-carbaldehyde
  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：

  在 咪唑 、 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 palladium dihydroxide 、 正丁基锂 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 pyridine-SO3 complex 、 4 A molecular sieve 、 四丁基氟化铵 、 氢气 、 三甲基铝 、 silver perchlorate 、 zinc trifluoromethanesulfonate 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 乙硫醇 作用下， 以 四氢呋喃 、 甲醇 、 硝基甲烷 、 二氯甲烷 、 溶剂黄146 、 二甲基亚砜 、 甲苯 为溶剂， 反应 76.33h， 生成 (1S,3R,8R,10S,12R,14R,15S,17R,19R)-15-[tert-butyl(dimethyl)silyl]oxy-8-[[tert-butyl(dimethyl)silyl]oxymethyl]-17-[3-[tert-butyl(diphenyl)silyl]oxypropyl]-10-methyl-2,9,13,18-tetraoxatetracyclo[10.8.0.03,10.014,19]icosan-7-one
  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

文献信息

• Total Synthesis of Brevetoxin A: Part 3: Construction of GHIJ and BCDE Ring Systems
  作者：K. C. Nicolaou、Guo-qiang Shi、Janet L. Gunzner、Peter Gärtner、Paul A. Wallace、Michael A. Ouellette、Shuhao Shi、Mark E. Bunnage、Konstantinos A. Agrios、Chris A. Veale、Chan-Kou Hwang、John Hutchinson、C. V. C. Prasad、William W. Ogilvie、Zhen Yang

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

  日期：1999.2.1

  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.