5-{(S)-[(3a'R,5'R,6'S,6a'R)-6'-benzyloxy-2',2'-dimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5'-yl](1H-indol-3-yl)methyl}-2,2-dimethyl-1,3-dioxane-4,6-dione | 1224111-92-5

• 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: 5-{(S)-[(3a'R,5'R,6'S,6a'R)-6'-benzyloxy-2',2'-dimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5'-yl](1H-indol-3-yl)methyl}-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 1224111-92-5
• 化学式: C₂₉H₃₁NO₈
• 分子量: 521.567
• InChiKey: BRCNFCDMSNTOMP-UFOFBUIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  105.31
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-{(S)-[(3a'R,5'R,6'S,6a'R)-6'-benzyloxy-2',2'-dimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5'-yl](1H-indol-3-yl)methyl}-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93%的产率得到(2R,3R,3aS,6S,7S,7aR)-2,3-dihydroxy-2,3-di-O-isopropylidene-7-(1H-indol-3-yl)-5-oxo-hexahydro-2H-furo[3,2-b]pyran-6-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
• 作为产物：
  描述：

  吲哚 、 丙二酸环(亚)异丙酯 、 3-O-苄基-1,2-O-异亚丙基-Alpha-D-木质二醛糖 在 DL-脯氨酸 作用下， 以 乙腈 为溶剂， 以81%的产率得到5-{(S)-[(3a'R,5'R,6'S,6a'R)-6'-benzyloxy-2',2'-dimethyl-dihydro-5H-furo[3,2-d][1,3]dioxol-5'-yl](1H-indol-3-yl)methyl}-2,2-dimethyl-1,3-dioxane-4,6-dione
  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