(3S,4S,5S)-4-(1H-indol-3-yl)-2-oxo-5-[(1'S,2'S)-1',2',3'-trihydroxypropan-1'-yl]-tetrahydrofuran-3-carboxylic acid | 1224111-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3S,4S,5S)-4-(1H-indol-3-yl)-2-oxo-5-[(1'S,2'S)-1',2',3'-trihydroxypropan-1'-yl]-tetrahydrofuran-3-carboxylic acid
• 英文别名: (3S,4S,5S)-4-(1H-indol-3-yl)-2-oxo-5-[(1S,2S)-1,2,3-trihydroxypropyl]oxolane-3-carboxylic acid
• CAS: 1224111-95-8
• 化学式: C₁₆H₁₇NO₇
• 分子量: 335.313
• InChiKey: OVMPXJBEOJWOIY-NDKCEZKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  140
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (1'S,2'S,3'R,4'S)-5-[2',3'-bis(benzyloxy)-4',5'-dihydroxy-1'-(1H-indol-3-yl)-4',5'-di-O-isopropylidene-pentan-1'-yl]-2,2-dimethyl-1,3-dioxane-4,6-dione 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以95%的产率得到(3S,4S,5S)-4-(1H-indol-3-yl)-2-oxo-5-[(1'S,2'S)-1',2',3'-trihydroxypropan-1'-yl]-tetrahydrofuran-3-carboxylic acid
  参考文献：
  名称：

  Diastereoselective trimolecular condensation between indole, Meldrum’s acid and chiral sugar-derived aldehydes

  摘要：

  The trimolecular condensation of indole, Meldrum's acid and chiral, sugar-derived aldehydes took place in good yield and high diastereoselectivity. The absolute configuration of the alpha-carbon of the chiral aldehydes ensured a predictable diastereocontrol of the newly created stereogenic centre except for (3aR,5S,6S,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydrofuro[3,2-d][1,3]dioxole-5-carbaldehyde 3i. In this case, the opposite stereochemistry may be explained by a less congested conformer of the Knoevenagel-adduct intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.017