(S)-4-((tert-butyldimethylsilyl)oxy)-2-((4R,6S)-2,2-dimethyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)-2-((triethylsilyl)oxy)butanal | 1309675-26-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-4-((tert-butyldimethylsilyl)oxy)-2-((4R,6S)-2,2-dimethyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)-2-((triethylsilyl)oxy)butanal
• 英文别名: (2S)-4-[tert-butyl(dimethyl)silyl]oxy-2-[(4R,6S)-2,2-dimethyl-6-(2-trimethylsilylethynyl)-1,3-dioxan-4-yl]-2-triethylsilyloxybutanal
• CAS: 1309675-26-0
• 化学式: C₂₇H₅₄O₅Si₃
• 分子量: 542.979
• InChiKey: XPUSQGIODNVVSR-FKCDAAJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.15
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-((tert-butyldimethylsilyl)oxy)-2-((4R,6S)-2,2-dimethyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)-2-((triethylsilyl)oxy)butanal 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 2.67h， 生成 (R,E)-6-((tert-butyldimethylsilyl)oxy)-4-((4R,6S)-2,2-dimethyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)-4-((triethylsilyl)oxy)hex-2-enal
  参考文献：
  名称：

  Formal Synthesis of Leustroducsin B via Reformatsky/Claisen Condensation of Silyl Glyoxylates

  摘要：

  A formal synthesis of leustroducsin B has been completed. The synthesis relies upon a recently developed Reformatsky/Claisen condensation of silyl glyoxylates and enantioenriched beta-lactones that establishes two of the molecule's three core stereocenters and permits further elaboration to an intermediate in Imanishl's synthesis via reliable chemistry (Prasad reduction, asymmetric pentenylation, Mitsunobu inversion).

  DOI：

  10.1021/ol2011192
• 作为产物：
  描述：

  1-benzyl 4-ethyl 2-(3-hydroxy-5-(trimethylsilyl)pent-4-ynoyl)-2-((triethylsilyl)oxy)succinate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 camphor-10-sulfonic acid 、 二乙基甲氧基硼烷 、 三乙基硼氢化锂 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 17.0h， 生成 (S)-4-((tert-butyldimethylsilyl)oxy)-2-((4R,6S)-2,2-dimethyl-6-((trimethylsilyl)ethynyl)-1,3-dioxan-4-yl)-2-((triethylsilyl)oxy)butanal
  参考文献：
  名称：

  Formal Synthesis of Leustroducsin B via Reformatsky/Claisen Condensation of Silyl Glyoxylates

  摘要：

  A formal synthesis of leustroducsin B has been completed. The synthesis relies upon a recently developed Reformatsky/Claisen condensation of silyl glyoxylates and enantioenriched beta-lactones that establishes two of the molecule's three core stereocenters and permits further elaboration to an intermediate in Imanishl's synthesis via reliable chemistry (Prasad reduction, asymmetric pentenylation, Mitsunobu inversion).

  DOI：

  10.1021/ol2011192

文献信息

• Formal Synthesis of Leustroducsin B via Reformatsky/Claisen Condensation of Silyl Glyoxylates
  作者：Stephen N. Greszler、Justin T. Malinowski、Jeffrey S. Johnson

  DOI：10.1021/ol2011192

  日期：2011.6.17

  A formal synthesis of leustroducsin B has been completed. The synthesis relies upon a recently developed Reformatsky/Claisen condensation of silyl glyoxylates and enantioenriched beta-lactones that establishes two of the molecule's three core stereocenters and permits further elaboration to an intermediate in Imanishl's synthesis via reliable chemistry (Prasad reduction, asymmetric pentenylation, Mitsunobu inversion).