maremycin B S-oxide | 1356133-13-5

• 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: maremycin B S-oxide
• 英文别名: (3S,6R)-3-[(1R)-1-[(3R)-3-hydroxy-1-methyl-2-oxoindol-3-yl]ethyl]-6-(methylsulfinylmethyl)piperazine-2,5-dione
• CAS: 1356133-13-5
• 化学式: C₁₇H₂₁N₃O₅S
• 分子量: 379.437
• InChiKey: SRLGBQOCPROCJP-KKDZFZDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  maremycin B S-oxide 以 甲醇 为溶剂， 反应 0.5h， 以75%的产率得到(1''S,3'R)-3-[1-(3-hydroxy-1-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl)ethyl]6-methylenepiperazine-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 、 甲醇 、 4-二甲氨基吡啶 、 sodium periodate 、 草酰氯 、 acetyl hypobromite 、 pyridine hydrofluoride 、 氧气 、 silica gel 、 silver nitrate 、 溶剂黄146 、 二甲基亚砜 、 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 、 锌 、 苯酚 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 正己烷 、 二氯甲烷 、 对二甲苯 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 328.17h， 生成 maremycin B S-oxide
  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

• 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.