Benzoic acid (S)-3-benzyloxy-1-methyl-2-oxo-propyl ester | 164145-51-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Benzoic acid (S)-3-benzyloxy-1-methyl-2-oxo-propyl ester
• 英文别名: 2-Butanone, 3-(benzoyloxy)-1-(phenylmethoxy)-, (3S)-；[(2S)-3-oxo-4-phenylmethoxybutan-2-yl] benzoate
• CAS: 164145-51-1
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: IOVJOJNYPDVELU-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  异丁醛 、 Benzoic acid (S)-3-benzyloxy-1-methyl-2-oxo-propyl ester 在 二甲基十二/十四烷基叔胺 、 氯代二环己基硼烷 、 双氧水 作用下， 生成 (2S,4R,5R)-2-Benzoyloxy-4-benzyloxy-5-hydroxy-6-methylheptan-3-one
  参考文献：
  名称：

  Studies in polypropionate synthesis: High π-face selectivity in syn and anti aldol reactions of chiral boron enolates of lactate-derived ketones

  摘要：

  Use of (c)Hex(2)BCl/Me(2)NEt in the aldol reactions of the alpha'-benzoyloxy ketone 7 with aldehydes leads to high stereoselectivity (97-99.5% ds) for the crystalline anti adducts 11. Under similar conditions, the corresponding benzyl ether 6 favours formation of the syn adducts 9.

  DOI：

  10.1016/0040-4039(94)88434-x
• 作为产物：
  描述：

  苯甲酸酐 、 (3S)-3-hydroxy-1-phenylmethoxybutan-2-one 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 Benzoic acid (S)-3-benzyloxy-1-methyl-2-oxo-propyl ester
  参考文献：
  名称：

  Polyketide Synthesis Using the Boron-Mediated, anti-Aldol Reactions of Lactate-Derived Ketones: Total Synthesis of (-)-ACRL Toxin IIIB

  摘要：

  The boron-mediated, anti-selective, aldol reactions of ketone 2 (and related derivatives) proceed with high levels of asymmetric induction, diastereoselectivities of up to 200:1 in favour of the aldol adducts 4 are obtained with achiral aldehydes and reagent control operates with chiral aldehydes. These lactate-derived ketones provide a versatile chiral auxiliary for the synthesis of beta-hydroxy carbonyl compounds. Oxidative removal of the auxiliary provides enantiomerically pure aldehydes 5, while reductive deoxygenation gives the corresponding ethyl ketones 6. This practical asymmetric methodology for generating anti-aldols is illustrated by an efficient total synthesis of (-)-ACRL toxin IIIB (7), which proceeds in 15 steps from 2 with 21% overall yield and 88% diastereoselectivity.

  DOI：

  10.1055/s-1998-5929

文献信息

• Studies in polypropionate synthesis: High π-face selectivity in syn and anti aldol reactions of chiral boron enolates of lactate-derived ketones
  作者：Ian Paterson、Debra J. Wallace、Silvia M. Velázquez

  DOI：10.1016/0040-4039(94)88434-x

  日期：1994.11

  Use of (c)Hex(2)BCl/Me(2)NEt in the aldol reactions of the alpha'-benzoyloxy ketone 7 with aldehydes leads to high stereoselectivity (97-99.5% ds) for the crystalline anti adducts 11. Under similar conditions, the corresponding benzyl ether 6 favours formation of the syn adducts 9.
• Polyketide Synthesis Using the Boron-Mediated, anti-Aldol Reactions of Lactate-Derived Ketones: Total Synthesis of (-)-ACRL Toxin IIIB
  作者：Ian Paterson

  DOI：10.1055/s-1998-5929

  日期：1998.3

  The boron-mediated, anti-selective, aldol reactions of ketone 2 (and related derivatives) proceed with high levels of asymmetric induction, diastereoselectivities of up to 200:1 in favour of the aldol adducts 4 are obtained with achiral aldehydes and reagent control operates with chiral aldehydes. These lactate-derived ketones provide a versatile chiral auxiliary for the synthesis of beta-hydroxy carbonyl compounds. Oxidative removal of the auxiliary provides enantiomerically pure aldehydes 5, while reductive deoxygenation gives the corresponding ethyl ketones 6. This practical asymmetric methodology for generating anti-aldols is illustrated by an efficient total synthesis of (-)-ACRL toxin IIIB (7), which proceeds in 15 steps from 2 with 21% overall yield and 88% diastereoselectivity.