(2R,3R,4R,6S,10R,11R)-2-(tert-Butyl-diphenyl-silanyloxy)-3,11-dihydroxy-4,6,10,12-tetramethyl-tridecane-5,9-dione | 735317-52-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (2R,3R,4R,6S,10R,11R)-2-(tert-Butyl-diphenyl-silanyloxy)-3,11-dihydroxy-4,6,10,12-tetramethyl-tridecane-5,9-dione
• 英文别名: (2R,3R,4R,6S,10R,11R)-2-[tert-butyl(diphenyl)silyl]oxy-3,11-dihydroxy-4,6,10,12-tetramethyltridecane-5,9-dione
• CAS: 735317-52-9
• 化学式: C₃₃H₅₀O₅Si
• 分子量: 554.842
• InChiKey: OSLVWVCQHQSYOS-RIDJGIGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.16
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基丙烷 、 (2R,3R,4R,6S,10R,11R)-2-(tert-Butyl-diphenyl-silanyloxy)-3,11-dihydroxy-4,6,10,12-tetramethyl-tridecane-5,9-dione 在 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 、 对甲苯磺酸 作用下， 以 乙腈 为溶剂， 反应 49.0h， 以71%的产率得到tert-Butyl-((R)-1-{(4R,5S,6S)-6-[(S)-3-((4R,5S,6R)-6-isopropyl-2,2,5-trimethyl-[1,3]dioxan-4-yl)-1-methyl-propyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-ethoxy)-diphenyl-silane
  参考文献：
  名称：

  Stereochemically Rich Pentaketides from Bis(isoxazolines):  A General Strategy for Efficient Polyketide Synthesis

  摘要：

  A strategy based on diastereoselective dipolar cycloaddition reaction of nitrile oxides and allylic alcoholates has been applied to the synthesis of bis(isoxazolines) that are precursors to polyketide fragments. These intermediates can be elaborated into protected polyols by chemoselective reductive opening of each isoxazoline sequentially or, alternatively, both simultaneously, potentially providing access to all stereoisomers of this carbon skeleton.

  DOI：

  10.1021/ol0490633
• 作为产物：
  描述：

  (R)-(-)-(Z)-pent-3-en-2-ol 在 palladium on activated charcoal 、 镍 咪唑 、 ammonium heptamolybdate 、 次氯酸叔丁酯 、 水 、 氢气 、 双氧水 、 硼酸 、 双(三甲基硅烷基)氨基钾 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.5h， 生成 (2R,3R,4R,6S,10R,11R)-2-(tert-Butyl-diphenyl-silanyloxy)-3,11-dihydroxy-4,6,10,12-tetramethyl-tridecane-5,9-dione
  参考文献：
  名称：

  Stereochemically Rich Pentaketides from Bis(isoxazolines):  A General Strategy for Efficient Polyketide Synthesis

  摘要：

  A strategy based on diastereoselective dipolar cycloaddition reaction of nitrile oxides and allylic alcoholates has been applied to the synthesis of bis(isoxazolines) that are precursors to polyketide fragments. These intermediates can be elaborated into protected polyols by chemoselective reductive opening of each isoxazoline sequentially or, alternatively, both simultaneously, potentially providing access to all stereoisomers of this carbon skeleton.

  DOI：

  10.1021/ol0490633

文献信息

• Stereochemically Rich Pentaketides from Bis(isoxazolines):  A General Strategy for Efficient Polyketide Synthesis
  作者：Lee D. Fader、Erick M. Carreira

  DOI：10.1021/ol0490633

  日期：2004.7.1

  A strategy based on diastereoselective dipolar cycloaddition reaction of nitrile oxides and allylic alcoholates has been applied to the synthesis of bis(isoxazolines) that are precursors to polyketide fragments. These intermediates can be elaborated into protected polyols by chemoselective reductive opening of each isoxazoline sequentially or, alternatively, both simultaneously, potentially providing access to all stereoisomers of this carbon skeleton.