(2R)-2-[(2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-tris(trimethylsilyl)silyloxypentyl]-2,3-dihydropyran-6-one | 934297-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R)-2-[(2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-tris(trimethylsilyl)silyloxypentyl]-2,3-dihydropyran-6-one
• CAS: 934297-85-5
• 化学式: C₂₅H₅₆O₄Si₅
• 分子量: 561.145
• InChiKey: OXSGIVFOCBBQGO-ZRBLBEILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.63
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R)-2-[(2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-tris(trimethylsilyl)silyloxypentyl]-2,3-dihydropyran-6-one 在 吡啶 、 氢氟酸 作用下， 以 四氢呋喃 为溶剂， 反应 11.0h， 生成 (+)-cryptocarya diacetate
  参考文献：
  名称：

  “Super Silyl” Group for Diastereoselective Sequential Reactions:  Access to Complex Chiral Architecture in One Pot

  摘要：

  We have shown that the tris(trimethylsilyl)silyl (TTMSS) silyl enol ether of acetaldehyde undergoes aldehyde cross-aldol reactions with high selectivity and the extremely low catalyst loading (0.05 mol % of HNTf2) allows for one-pot sequential reactions where acidic or basic nucleophiles can be subsequently added. Various ketone-derived silyl enol ethers, Grignard reagents, and dienes succeeded, generating relatively complex molecular architectures in a single step. This represents the first case where, in a single pot, highly acidic conditions followed by very basic conditions were tolerated to give products with high diastereoselectivities and good yields.

  DOI：

  10.1021/ja0693542
• 作为产物：
  描述：

  三(三甲基硅基)氧乙烯基硅烷 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 双三氟甲烷磺酰亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (2R)-2-[(2R,4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-tris(trimethylsilyl)silyloxypentyl]-2,3-dihydropyran-6-one
  参考文献：
  名称：

  “Super Silyl” Group for Diastereoselective Sequential Reactions:  Access to Complex Chiral Architecture in One Pot

  摘要：

  We have shown that the tris(trimethylsilyl)silyl (TTMSS) silyl enol ether of acetaldehyde undergoes aldehyde cross-aldol reactions with high selectivity and the extremely low catalyst loading (0.05 mol % of HNTf2) allows for one-pot sequential reactions where acidic or basic nucleophiles can be subsequently added. Various ketone-derived silyl enol ethers, Grignard reagents, and dienes succeeded, generating relatively complex molecular architectures in a single step. This represents the first case where, in a single pot, highly acidic conditions followed by very basic conditions were tolerated to give products with high diastereoselectivities and good yields.

  DOI：

  10.1021/ja0693542

文献信息

• “Super Silyl” Group for Diastereoselective Sequential Reactions:  Access to Complex Chiral Architecture in One Pot
  作者：Matthew B. Boxer、Hisashi Yamamoto

  DOI：10.1021/ja0693542

  日期：2007.3.1

  We have shown that the tris(trimethylsilyl)silyl (TTMSS) silyl enol ether of acetaldehyde undergoes aldehyde cross-aldol reactions with high selectivity and the extremely low catalyst loading (0.05 mol % of HNTf2) allows for one-pot sequential reactions where acidic or basic nucleophiles can be subsequently added. Various ketone-derived silyl enol ethers, Grignard reagents, and dienes succeeded, generating relatively complex molecular architectures in a single step. This represents the first case where, in a single pot, highly acidic conditions followed by very basic conditions were tolerated to give products with high diastereoselectivities and good yields.