2-[(3R,5R)-3,6-Bis-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-hexanoylaminooxy]-propionic acid tert-butyl ester | 604003-41-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-[(3R,5R)-3,6-Bis-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-hexanoylaminooxy]-propionic acid tert-butyl ester
• CAS: 604003-41-0
• 化学式: C₂₉H₅₇N₃O₉Si
• 分子量: 619.872
• InChiKey: GMPGBQKQSORWOP-RWLBOTFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  42.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  150.52
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-[(3R,5R)-3,6-Bis-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-hexanoylaminooxy]-propionic acid tert-butyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 2-[[(3R,5R)-3,6-diamino-5-hydroxyhexanoyl]amino]oxypropanoic acid
  参考文献：
  名称：

  N- and C-terminal modifications of negamycin

  摘要：

  Negamycin 1 is a bactericidal antibiotic with activity against Gram-negative bacteria, and served as a template in an antibiotic discovery program. An orthogonally protected beta-amino acid derivative 3a was synthesized and used in parallel synthesis of negamycin derivatives on solid support. This advanced intermediate was also used for N- and C-terminal modifications using solution-phase methodologies. The N-terminal modifications have resulted in the identification of active analogues, whereas the C-terminal modifications resulted in complete loss of antibacterial activity. The N-methyl negamycin analogue, 19a, inhibits protein synthesis (IC50 = 2.3 muM), has antibacterial activity (Escherichia coli, MIC = 16 mug/mL), and is efficacious in an E. coli murine septicemia model (ED50 = 16.3 mg/kg). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00393-7
• 作为产物：
  描述：

  2-溴丙酸叔丁酯 在 sodium hydride 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(3R,5R)-3,6-Bis-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-hexanoylaminooxy]-propionic acid tert-butyl ester
  参考文献：
  名称：

  N- and C-terminal modifications of negamycin

  摘要：

  Negamycin 1 is a bactericidal antibiotic with activity against Gram-negative bacteria, and served as a template in an antibiotic discovery program. An orthogonally protected beta-amino acid derivative 3a was synthesized and used in parallel synthesis of negamycin derivatives on solid support. This advanced intermediate was also used for N- and C-terminal modifications using solution-phase methodologies. The N-terminal modifications have resulted in the identification of active analogues, whereas the C-terminal modifications resulted in complete loss of antibacterial activity. The N-methyl negamycin analogue, 19a, inhibits protein synthesis (IC50 = 2.3 muM), has antibacterial activity (Escherichia coli, MIC = 16 mug/mL), and is efficacious in an E. coli murine septicemia model (ED50 = 16.3 mg/kg). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00393-7