(3R,5R)-3,6-Bis-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-hexanoic acid | 604003-40-9

• 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: (3R,5R)-3,6-Bis-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-hexanoic acid
• CAS: 604003-40-9
• 化学式: C₂₂H₄₄N₂O₇Si
• 分子量: 476.686
• InChiKey: HBHAYRNCASUALJ-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  32.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  123.19
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3R,5R)-3,6-Bis-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-hexanoic acid 在 盐酸 、 sodium hydroxide 、 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 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 (2R)-1-[[(3R,5R)-3,6-diamino-5-hydroxyhexanoyl]amino]pyrrolidine-2-carboxylic 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：

  ((R)-2-Iodomethyl-6-oxo-tetrahydro-pyran-4-yl)-carbamic acid tert-butyl ester 在 palladium on activated charcoal 吡啶 、 咪唑 、 氢氧化钾 、 lithium hydroxide 、 sodium azide 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 76.0h， 生成 (3R,5R)-3,6-Bis-tert-butoxycarbonylamino-5-(tert-butyl-dimethyl-silanyloxy)-hexanoic 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