((R)-2-Iodomethyl-6-oxo-tetrahydro-pyran-4-yl)-carbamic acid tert-butyl ester | 551964-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: ((R)-2-Iodomethyl-6-oxo-tetrahydro-pyran-4-yl)-carbamic acid tert-butyl ester
• CAS: 551964-17-1
• 化学式: C₁₁H₁₈INO₄
• 分子量: 355.173
• InChiKey: SPHUHQWORBJEFC-GVHYBUMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ((R)-2-Iodomethyl-6-oxo-tetrahydro-pyran-4-yl)-carbamic acid tert-butyl ester 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 ((R)-2-Azidomethyl-6-oxo-tetrahydro-pyran-4-yl)-carbamic 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
• 作为产物：
  描述：

  Boc-(R)-3-氨基-5-己烯酸 在 碘 、 碳酸氢钠 、 potassium iodide 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以88%的产率得到((R)-2-Iodomethyl-6-oxo-tetrahydro-pyran-4-yl)-carbamic 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