(3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde | 1141365-72-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde
• 英文别名: 2-[(3S,4S)-4-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-2-methoxy-3-methyloxolan-2-yl]acetaldehyde
• CAS: 1141365-72-1
• 化学式: C₂₆H₃₆O₄Si
• 分子量: 440.655
• InChiKey: NCNZGAMTKGGIHQ-SMWUWQHRSA-N

物化性质

• 沸点：
  494.1±43.0 °C(predicted)
• 密度：
  1.06±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  (3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde 、 2,6-dihydroxy-4-[(2R)-2-hydroxyheptyl]benzoic acid 在 Dowex 50WX₈-400-H⁺ ion exchange resin 作用下， 以 甲醇 为溶剂， 反应 60.0h， 生成 、
  参考文献：
  名称：

  Synthesis of (−)-Berkelic Acid

  摘要：

  AbstractAn extremophilic challenge: Stereospecific condensation of a fully functionalized ketal aldehyde and a 2,6‐dihydroxybenzoic acid is the key step in the synthesis of (−)‐berkelic acid confirming Fürstner's reassignment of the stereochemistry at C18 and C19, establishing the absolute stereochemistry, and tentatively assigning the stereochemistry at C22.magnified image

  DOI：

  10.1002/anie.200805488
• 作为产物：
  描述：

  (3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxy-3-methyl-2-furanethanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到(3S,4S)-4-[2-[(1,1-dimethylethyl)diphenylsilyloxy]ethyl]tetrahydro-2-methoxyl-3-methyl-2-furanacetaldehyde
  参考文献：
  名称：

  Synthesis of (−)-Berkelic Acid

  摘要：

  AbstractAn extremophilic challenge: Stereospecific condensation of a fully functionalized ketal aldehyde and a 2,6‐dihydroxybenzoic acid is the key step in the synthesis of (−)‐berkelic acid confirming Fürstner's reassignment of the stereochemistry at C18 and C19, establishing the absolute stereochemistry, and tentatively assigning the stereochemistry at C22.magnified image

  DOI：

  10.1002/anie.200805488

文献信息

• Introduction of the (−)-Berkelic Acid Side Chain and Assignment of the C-22 Stereochemistry
  作者：Xiaoxing Wu、Jingye Zhou、Barry B. Snider

  DOI：10.1021/jo901221a

  日期：2009.8.21

  oxidized and deprotected to complete the synthesis of (−)-berkelic acid and (−)-22-epi-berkelic acid. This synthesis establishes the absolute stereochemistry and assigns the stereochemistry at C-22. A biosynthetic pathway is proposed that is consistent with the known absolute stereochemistry at the quaternary carbon of spiciferone A, spicifernin, and berkelic acid and provides a simple explanation for

  醛与三甲基甲硅烷基乙烯酮缩醛的 Kiyooka 羟醛缩合反应和由N -Ts-( S )-缬氨酸制备的恶唑硼烷酮得到四种可能的羟醛加合物中的两种，它们被氧化和脱保护以完成 (-)-berkelic 的合成酸和 (-)-22- epi- berkelic 酸。该合成建立了绝对立体化学并将立体化学指定为 C-22。提出了一种生物合成途径，该途径与已知的 spiciferone A、spicifernin 和 berkelic 酸的季碳上的绝对立体化学一致，并为 spicifernin 和 berkelic 酸的 C-18 和 C-19 的不同立体化学提供了简单的解释。
• Synthesis of (−)-Berkelic Acid
  作者：Xiaoxing Wu、Jingye Zhou、Barry B. Snider

  DOI：10.1002/anie.200805488

  日期：2009.2.2

  AbstractAn extremophilic challenge: Stereospecific condensation of a fully functionalized ketal aldehyde and a 2,6‐dihydroxybenzoic acid is the key step in the synthesis of (−)‐berkelic acid confirming Fürstner's reassignment of the stereochemistry at C18 and C19, establishing the absolute stereochemistry, and tentatively assigning the stereochemistry at C22.magnified image