methyl 3-[tert-butyl(dimethyl)silyl]oxy-3-methyl-4-[(2S,3R,5S,6R)-6-methyl-3,5-bis(phenylmethoxy)-6-[2-(trifluoromethylsulfonyloxy)prop-2-enyl]oxan-2-yl]butanoate | 205864-97-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-[tert-butyl(dimethyl)silyl]oxy-3-methyl-4-[(2S,3R,5S,6R)-6-methyl-3,5-bis(phenylmethoxy)-6-[2-(trifluoromethylsulfonyloxy)prop-2-enyl]oxan-2-yl]butanoate
• CAS: 205864-97-7
• 化学式: C₃₆H₅₁F₃O₉SSi
• 分子量: 744.942
• InChiKey: YQJQDHWXRDCEFB-PSLAYBBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  50
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  methyl 3-[tert-butyl(dimethyl)silyl]oxy-3-methyl-4-[(2S,3R,5S,6R)-6-methyl-3,5-bis(phenylmethoxy)-6-[2-(trifluoromethylsulfonyloxy)prop-2-enyl]oxan-2-yl]butanoate 在 palladium on activated charcoal 、 Wilkinson's catalyst 、 四(三苯基膦)钯 4-二甲氨基吡啶 、 lithium hydroxide 、 锌铜偶 、 双[Α,Α-双(三氟甲基)苯甲醇合]二苯硫 、 氨 、 水 、 氢气 、 lithium 、 氟化氢吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 31.25h， 生成 (4S,5aS,6aR,8R,12aS,13aR)-4,6a,8-Trimethyl-dodecahydro-1,6,12-trioxa-cyclohepta[4,5]benzo[1,2]cyclooctene-2,11-dione
  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：

  N-苯基双(三氟甲烷磺酰)亚胺 、 4-[(2S,3R,5S,6R)-3,5-Bis-benzyloxy-6-methyl-6-(2-oxo-propyl)-tetrahydro-pyran-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyric acid methyl ester 在 sodium hexamethyldisilazane 作用下， 生成 methyl 3-[tert-butyl(dimethyl)silyl]oxy-3-methyl-4-[(2S,3R,5S,6R)-6-methyl-3,5-bis(phenylmethoxy)-6-[2-(trifluoromethylsulfonyloxy)prop-2-enyl]oxan-2-yl]butanoate
  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.