(1S,4S,5R,9S,12S,13R,17S,20S,21R)-4,12,20-tris(hydroxymethyl)-25,26,27-trioxa-3,11,19-triazatetracyclo[19.3.1.15,9.113,17]heptacosane-2,10,18-trione | 444687-49-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (1S,4S,5R,9S,12S,13R,17S,20S,21R)-4,12,20-tris(hydroxymethyl)-25,26,27-trioxa-3,11,19-triazatetracyclo[19.3.1.15,9.113,17]heptacosane-2,10,18-trione
• CAS: 444687-49-4
• 化学式: C₂₄H₃₉N₃O₉
• 分子量: 513.588
• InChiKey: ARCUVAGEHMOWLA-USSSXZFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  176
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  硫代乙酸 、 (1S,4S,5R,9S,12S,13R,17S,20S,21R)-4,12,20-tris(hydroxymethyl)-25,26,27-trioxa-3,11,19-triazatetracyclo[19.3.1.15,9.113,17]heptacosane-2,10,18-trione 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 以80%的产率得到S-[[(1R,2R,5S,9R,10R,13S,17R,18R,21S)-10,18-bis(acetylsulfanylmethyl)-4,12,20-trioxo-25,26,27-trioxa-3,11,19-triazatetracyclo[19.3.1.15,9.113,17]heptacosan-2-yl]methyl] ethanethioate
  参考文献：
  名称：

  Synthesis and Structure of Preorganized, C₃-Symmetric Trilactam Scaffolds with Convergently Oriented (S)-Acetylthiomethyl Appendages

  摘要：

  Efficient modular synthesis of conformationally preorganized, C-3-symmetric trilactams is reported. The allyl acetate cyclization substrate was synthesized in five steps from Gamer's L-serine-derived aldehyde. After chiral ligand-mediated palladium cyclization, the resulting vinyl hydropyran was transformed into the orthogonally protected amino acids for iterative coupling. The final macrolactamization was accomplished using EDCI/HOBt or HATU/HOAt under high dilution conditions.

  DOI：

  10.1021/ol0261480
• 作为产物：
  描述：

  (2S,6R)-6-[(S)-1-({(2S,6R)-6-[(S)-1-Benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carbonyl}-amino)-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-tetrahydro-pyran-2-carboxylic acid ethyl ester 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 N-羟基-7-氮杂苯并三氮唑 、 氢气 、 1-羟基苯并三唑 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 124.0h， 生成 (1S,4S,5R,9S,12S,13R,17S,20S,21R)-4,12,20-tris(hydroxymethyl)-25,26,27-trioxa-3,11,19-triazatetracyclo[19.3.1.15,9.113,17]heptacosane-2,10,18-trione
  参考文献：
  名称：

  Synthesis and Structure of Preorganized, C₃-Symmetric Trilactam Scaffolds with Convergently Oriented (S)-Acetylthiomethyl Appendages

  摘要：

  Efficient modular synthesis of conformationally preorganized, C-3-symmetric trilactams is reported. The allyl acetate cyclization substrate was synthesized in five steps from Gamer's L-serine-derived aldehyde. After chiral ligand-mediated palladium cyclization, the resulting vinyl hydropyran was transformed into the orthogonally protected amino acids for iterative coupling. The final macrolactamization was accomplished using EDCI/HOBt or HATU/HOAt under high dilution conditions.

  DOI：

  10.1021/ol0261480