(2R,3S)-5-((tert-butyldimethylsilyl)oxy)-1-(2-ethyl-1H-pyrrol-1-yl)-2,3-dihydroxy-4,4-dimethylpentan-1-one | 1449799-28-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: (2R,3S)-5-((tert-butyldimethylsilyl)oxy)-1-(2-ethyl-1H-pyrrol-1-yl)-2,3-dihydroxy-4,4-dimethylpentan-1-one
• 英文别名: (2R,3S)-5-[tert-butyl(dimethyl)silyl]oxy-1-(2-ethylpyrrol-1-yl)-2,3-dihydroxy-4,4-dimethylpentan-1-one
• CAS: 1449799-28-3
• 化学式: C₁₉H₃₅NO₄Si
• 分子量: 369.577
• InChiKey: VKPWRKIAVZKHIT-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  71.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(benzyloxy)-1-(2-ethyl-1H-pyrrol-1-yl)ethanone 在 (R,R)-(-)-2,6-bis[2-(hydroxyldiphenylmethyl)-1-pyrrolidinyl-methyl]-4-methylphenole 、 diethylzinc 、 三溴化硼 作用下， 以 四氢呋喃 、 正己烷 、 正庚烷 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (2R,3S)-5-((tert-butyldimethylsilyl)oxy)-1-(2-ethyl-1H-pyrrol-1-yl)-2,3-dihydroxy-4,4-dimethylpentan-1-one 、 (2S,3R)-5-((tert-butyldimethylsilyl)oxy)-1-(2-ethyl-1H-pyrrol-1-yl)-2,3-dihydroxy-4,4-dimethylpentan-1-one 、 5-((tert-butyldimethylsilyl)oxy)-1-(2-ethyl-1H-pyrrol-1-yl)-2,3-dihydroxy-4,4-dimethylpentan-1-one
  参考文献：
  名称：

  Dinuclear Zinc–ProPhenol-Catalyzed Enantioselective α-Hydroxyacetate Aldol Reaction with Activated Ester Equivalents

  摘要：

  An enantioselective alpha-hydroxyacetate aldol reaction that employs N-acetyl pyrroles as activated ester equivalents and generates syn 1,2-diols in good yield and diastereoselectivity is reported. This dinuclear zinc-ProPhenol-catalyzed transformation proceeds with high enantioselectivity with a wide variety of substrates including aryl, alyl, and alkenyl aldehydes. The resulting alpha,beta-dihydroxy activated esters are versatile intermediates for the synthesis of a variety of carboxylic acid derivatives including amides, esters, and unsymmetrical ketones.

  DOI：

  10.1021/ol402081p