(2S,3R,6R)-ethyl 4-t-buthyldimethylsiloxy-3,6-dihydro-3-methyl-6-((E)-prop-1-enyl)-2H-pyran-2-carboxylate | 1187319-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2S,3R,6R)-ethyl 4-t-buthyldimethylsiloxy-3,6-dihydro-3-methyl-6-((E)-prop-1-enyl)-2H-pyran-2-carboxylate
• 英文别名: ethyl (2S,3R,6R)-4-[tert-butyl(dimethyl)silyl]oxy-3-methyl-6-[(E)-prop-1-enyl]-3,6-dihydro-2H-pyran-2-carboxylate
• CAS: 1187319-20-5
• 化学式: C₁₈H₃₂O₄Si
• 分子量: 340.535
• InChiKey: IPWILMYVUCPQOX-HBLFGVLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙醛酸乙酯 、 ((4E,6E)-octa-2,4,6-trien-3-yloxy)(t-butyl)dimethylsilane 在 (R_a)-4-hydroxy-2,6-diphenyldinaphtho[1,3,2]dioxaphosphepine 4-oxide 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以75%的产率得到(2S,3R,6R)-ethyl 4-t-buthyldimethylsiloxy-3,6-dihydro-3-methyl-6-((E)-prop-1-enyl)-2H-pyran-2-carboxylate
  参考文献：
  名称：

  Chiral Phosphoric Acid-Governed Anti-Diastereoselective and Enantioselective Hetero-Diels−Alder Reaction of Glyoxylate

  摘要：

  A highly enantioselective anti-diastereoselective hetero-Diets-Alder reaction between a glyoxylate and siloxy- or methoxydienes using a chiral phosphoric acid catalyst that possesses less bulky phenyl groups at the 3 and 3' positions of binaphthyl has been developed. The diastereoselectivities presented are disparate to those previously reported for hetero-Diets-Alder reactions catalyzed by a chiral Lewis acid.

  DOI：

  10.1021/ja904749x

文献信息

• Chiral Phosphoric Acid-Governed Anti-Diastereoselective and Enantioselective Hetero-Diels−Alder Reaction of Glyoxylate
  作者：Norie Momiyama、Hideaki Tabuse、Masahiro Terada

  DOI：10.1021/ja904749x

  日期：2009.9.16

  A highly enantioselective anti-diastereoselective hetero-Diets-Alder reaction between a glyoxylate and siloxy- or methoxydienes using a chiral phosphoric acid catalyst that possesses less bulky phenyl groups at the 3 and 3' positions of binaphthyl has been developed. The diastereoselectivities presented are disparate to those previously reported for hetero-Diets-Alder reactions catalyzed by a chiral Lewis acid.