(1'S,2'S,3'R,4'S)-5-[2',3',4',5'-tetrahydroxy-1'-(1H-indol-3-yl)-(2',3':4',5')-di-O-isopropylidene-pentan-1'-yl]-2,2-dimethyl-1,3-dioxane-4,6-dione | 1224111-84-5

• 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: (1'S,2'S,3'R,4'S)-5-[2',3',4',5'-tetrahydroxy-1'-(1H-indol-3-yl)-(2',3':4',5')-di-O-isopropylidene-pentan-1'-yl]-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 5-[(S)-[(4S,5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-(1H-indol-3-yl)methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 1224111-84-5
• 化学式: C₂₅H₃₁NO₈
• 分子量: 473.523
• InChiKey: UUAUENHWLGATMX-HNJRGHQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  105
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  甲醇 、 (1'S,2'S,3'R,4'S)-5-[2',3',4',5'-tetrahydroxy-1'-(1H-indol-3-yl)-(2',3':4',5')-di-O-isopropylidene-pentan-1'-yl]-2,2-dimethyl-1,3-dioxane-4,6-dione 在 盐酸 作用下， 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 methyl ester
  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 、 2,3:4,5-di-O-isopropylidene-L-arabinose 在 DL-脯氨酸 作用下， 以 乙腈 为溶剂， 以55%的产率得到(1'S,2'S,3'R,4'S)-5-[2',3',4',5'-tetrahydroxy-1'-(1H-indol-3-yl)-(2',3':4',5')-di-O-isopropylidene-pentan-1'-yl]-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

文献信息

• Diastereoselective trimolecular condensation between indole, Meldrum’s acid and chiral sugar-derived aldehydes
  作者：Emmanuel Dardennes、Stéphane Gérard、Christian Petermann、Janos Sapi

  DOI：10.1016/j.tetasy.2009.12.017

  日期：2010.2

  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.