methyl (2S,3S)-2-amino-3-(1-methyl-2-oxo-3H-indol-3-yl)butanoate | 1356133-07-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S,3S)-2-amino-3-(1-methyl-2-oxo-3H-indol-3-yl)butanoate
• CAS: 1356133-07-7
• 化学式: C₁₄H₁₈N₂O₃
• 分子量: 262.309
• InChiKey: XPKHSSUGLNDYKV-XWMUTSTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S,3S)-2-amino-3-(1-methyl-2-oxo-3H-indol-3-yl)butanoate 在 甲醇 、 氧气 、 silica gel 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 对二甲苯 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 11.17h， 生成 (3S,6R)-3-{(1R)-1-[(3S)-3-hydroxy-1-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl]ethyl}-6-[(methylsulfanyl)methyl]piperazine-2,5-dione
  参考文献：
  名称：

  Total synthesis of maremycins A, B, C1/C2, D1, and D2

  摘要：

  The total synthesis of maremycins A, B, C-1/C-2, D-1, and D-2 is achieved starting from the natural amino acids L-isoleucine and S-methyl-L-cysteine, in which the total synthesis of maremycins B, C-1/C-2, and D-2 is accomplished for the first time. The synthesis features a position-selective intramolecular bromination process for the synthesis of key chiral building block, a Pd-catalyzed indole synthesis for the preparation of (2S,3S)-beta-methyltryptophan and hydroxylation of oxindoles by molecular oxygen. In addition, the protocol for conversion of maremycins A and B to maremycins C and D was improved. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.118
• 作为产物：
  描述：

  (2S,3S)-methyl 3-methyl-2-(2,2,2-trifluoroacetamido)pentanoate 在 吡啶 、 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 草酰氯 、 acetyl hypobromite 、 pyridine hydrofluoride 、 silver nitrate 、 溶剂黄146 、 二甲基亚砜 、 锌 、 苯酚 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 293.0h， 生成 methyl (2S,3S)-2-amino-3-(1-methyl-2-oxo-3H-indol-3-yl)butanoate
  参考文献：
  名称：

  Total synthesis of maremycins A, B, C1/C2, D1, and D2

  摘要：

  The total synthesis of maremycins A, B, C-1/C-2, D-1, and D-2 is achieved starting from the natural amino acids L-isoleucine and S-methyl-L-cysteine, in which the total synthesis of maremycins B, C-1/C-2, and D-2 is accomplished for the first time. The synthesis features a position-selective intramolecular bromination process for the synthesis of key chiral building block, a Pd-catalyzed indole synthesis for the preparation of (2S,3S)-beta-methyltryptophan and hydroxylation of oxindoles by molecular oxygen. In addition, the protocol for conversion of maremycins A and B to maremycins C and D was improved. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.118

文献信息

• Synthesis of tryptophan-containing 2,5-diketopiperazines <i>via</i> sequential C–H activation: total syntheses of tryprostatin A, maremycins A and B
  作者：Xue-Song Yin、Wei-Yi Qi、Bing-Feng Shi

  DOI：10.1039/d1sc02343h

  日期：——

  subsequent C2-selective prenylation of the resulting 6-OMe-Trp by Pd/norbornene-promoted C–H activation led to the total synthesis of tryprostatin A in 12 linear steps from alanine with 25% overall yield. Meanwhile, total syntheses of maremycins A and B were successfully accomplished using a sequential Pd-catalyzed methylene C(sp3)–H methylation as the key step in 15 linear steps from alanine.

  吲哚 2,5-二酮哌嗪 (DKP) 是一种重要的代谢环二肽，含有色氨酸 (Trp) 单元，具有一系列有趣的生物活性。有趣的结构特征和不同的活动激发了对其有效合成的巨大努力。在此，我们报告了通过连续 C-H 激活策略合成三种含 Trp 的 DKP，即胰前列腺素 A 和马雷霉素 A 和 B 的统一策略的开发。关键的色氨酸骨架是通过Pd( II ) 催化的 β-甲基 C(sp 3)–H 单芳基化。随后通过 Pd/降冰片烯促进的 C-H 活化对所得 6-OMe-Trp 进行 C2 选择性异戊二烯化，导致在 12 个线性步骤中从丙氨酸全合成胰前列腺素 A，总产率为 25%。同时，使用连续 Pd 催化的亚甲基 C(sp 3 )-H 甲基化作为来自丙氨酸的 15 个线性步骤中的关键步骤，成功地完成了马雷霉素 A 和 B 的全合成。
• Total synthesis of maremycins A, B, C1/C2, D1, and D2
  作者：Yonghua Liu、Liangren Zhang、Yanxing Jia

  DOI：10.1016/j.tetlet.2011.11.118

  日期：2012.2

  The total synthesis of maremycins A, B, C-1/C-2, D-1, and D-2 is achieved starting from the natural amino acids L-isoleucine and S-methyl-L-cysteine, in which the total synthesis of maremycins B, C-1/C-2, and D-2 is accomplished for the first time. The synthesis features a position-selective intramolecular bromination process for the synthesis of key chiral building block, a Pd-catalyzed indole synthesis for the preparation of (2S,3S)-beta-methyltryptophan and hydroxylation of oxindoles by molecular oxygen. In addition, the protocol for conversion of maremycins A and B to maremycins C and D was improved. (C) 2011 Elsevier Ltd. All rights reserved.