[(2R,3S,5R,6S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[4-[(1S,3R,5S,6R,8S,11R,13S,14R)-5-[tert-butyl(dimethyl)silyl]oxy-11,13-dimethyl-14-phenylmethoxy-13-(2-phenylmethoxyethyl)-2,7,12-trioxatricyclo[9.4.0.03,8]pentadecan-6-yl]but-2-ynyl]-2-methyloxan-2-yl]methoxy-tert-butyl-dimethylsilane | 476687-95-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(2R,3S,5R,6S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[4-[(1S,3R,5S,6R,8S,11R,13S,14R)-5-[tert-butyl(dimethyl)silyl]oxy-11,13-dimethyl-14-phenylmethoxy-13-(2-phenylmethoxyethyl)-2,7,12-trioxatricyclo[9.4.0.03,8]pentadecan-6-yl]but-2-ynyl]-2-methyloxan-2-yl]methoxy-tert-butyl-dimethylsilane
• CAS: 476687-95-3
• 化学式: C₆₅H₁₁₂O₁₀Si₄
• 分子量: 1165.94
• InChiKey: VZYSACRVRCJHMG-UCKVTZAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.35
• 重原子数：
  79
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  [(2R,3S,5R,6S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[4-[(1S,3R,5S,6R,8S,11R,13S,14R)-5-[tert-butyl(dimethyl)silyl]oxy-11,13-dimethyl-14-phenylmethoxy-13-(2-phenylmethoxyethyl)-2,7,12-trioxatricyclo[9.4.0.03,8]pentadecan-6-yl]but-2-ynyl]-2-methyloxan-2-yl]methoxy-tert-butyl-dimethylsilane 在 ruthenium(IV) oxide sodium periodate 、 camphor-10-sulfonic acid 作用下， 以 甲醇 、 四氯化碳 、 水 、 乙腈 为溶剂， 生成 (1S,3R,5S,7R,8S,10R,13S,15R,17S,19R,21S,22R,24S,26R)-22-(hydroxymethyl)-17,26-dimethoxy-8,10,22-trimethyl-7-phenylmethoxy-8-(2-phenylmethoxyethyl)-4,9,14,18,23,27-hexaoxahexacyclo[13.12.0.03,13.05,10.017,26.019,24]heptacosan-21-ol
  参考文献：
  名称：

  Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin

  摘要：

  [GRAPHICS]The convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin was accomplished. This efficient convergent strategy was performed on the basis of the coupling of the acetylide of the A-ring and the triflate of the DEF-ring, oxidation of the alkyne to diketone, intramolecular diacetalization, and stereoselective reduction of the diacetal with Et3SiH-TMSOTf.

  DOI：

  10.1021/ol026804w
• 作为产物：
  描述：

  2-deoxy-D-ribose 在 4 Angstroem MS N-甲基吗啉 、 2,6-二甲基吡啶 、 titanium(IV) isopropylate 、 盐酸 、 叔丁基过氧化氢 、 9-borabicyclo[3.3.1]nonane dimer 、 samarium diiodide 、 pyridine-SO3 complex 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 叔丁基锂 、 sodium hexamethyldisilazane 、 4-甲基苯磺酸吡啶 、 四丁基碘化铵 、 sodium hydride 、 二异丁基氢化铝 、 碳酸氢钠 、 (-)-diethyl tartrate 、 三乙胺 、 sodium iodide 、 lithium diisopropyl amide 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 二氯甲烷 、 氯仿 、 水 、 二甲基亚砜 、 丙酮 、 甲苯 、 乙腈 为溶剂， 生成 [(2R,3S,5R,6S)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-6-[4-[(1S,3R,5S,6R,8S,11R,13S,14R)-5-[tert-butyl(dimethyl)silyl]oxy-11,13-dimethyl-14-phenylmethoxy-13-(2-phenylmethoxyethyl)-2,7,12-trioxatricyclo[9.4.0.03,8]pentadecan-6-yl]but-2-ynyl]-2-methyloxan-2-yl]methoxy-tert-butyl-dimethylsilane
  参考文献：
  名称：

  Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin

  摘要：

  [GRAPHICS]The convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin was accomplished. This efficient convergent strategy was performed on the basis of the coupling of the acetylide of the A-ring and the triflate of the DEF-ring, oxidation of the alkyne to diketone, intramolecular diacetalization, and stereoselective reduction of the diacetal with Et3SiH-TMSOTf.

  DOI：

  10.1021/ol026804w

文献信息

• Convergent Synthesis of the ABCDEF-Ring System of Yessotoxin and Adriatoxin
  作者：Keisuke Suzuki、Tadashi Nakata

  DOI：10.1021/ol026804w

  日期：2002.10.1

  [GRAPHICS]The convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin was accomplished. This efficient convergent strategy was performed on the basis of the coupling of the acetylide of the A-ring and the triflate of the DEF-ring, oxidation of the alkyne to diketone, intramolecular diacetalization, and stereoselective reduction of the diacetal with Et3SiH-TMSOTf.