[(2S,4R,5R,6S)-5-[tert-butyl(dimethyl)silyl]oxy-4,6-dimethyl-3-oxo-7-phenylmethoxyheptan-2-yl] benzoate | 207680-82-8

• 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: [(2S,4R,5R,6S)-5-[tert-butyl(dimethyl)silyl]oxy-4,6-dimethyl-3-oxo-7-phenylmethoxyheptan-2-yl] benzoate
• CAS: 207680-82-8
• 化学式: C₂₉H₄₂O₅Si
• 分子量: 498.735
• InChiKey: QWIYUXGOLGQMTE-RNLGNXJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(2S,4R,5R,6S)-5-[tert-butyl(dimethyl)silyl]oxy-4,6-dimethyl-3-oxo-7-phenylmethoxyheptan-2-yl] benzoate 在 盐酸 、 sodium tetrahydroborate 、 sodium periodate 、 锂硼氢 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.5h， 生成 (2S,3S,4S)-5-Benzyloxy-2,4-dimethylpentan-1,3-diol
  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
• 作为产物：
  描述：

  (2S)-2-(苯甲酰基氧基)-3-戊酮 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 [(2S,4R,5R,6S)-5-[tert-butyl(dimethyl)silyl]oxy-4,6-dimethyl-3-oxo-7-phenylmethoxyheptan-2-yl] benzoate
  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

• 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.