2,3-di-O-acetyl-4,6-dideoxy-α-D-xylo-hexopyranosyl trichloroacetimidate | 485809-87-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2,3-di-O-acetyl-4,6-dideoxy-α-D-xylo-hexopyranosyl trichloroacetimidate
• 英文别名: [(2R,3R,4S,6R)-3-acetyloxy-6-methyl-2-(2,2,2-trichloroethanimidoyl)oxyoxan-4-yl] acetate
• CAS: 485809-87-8
• 化学式: C₁₂H₁₆Cl₃NO₆
• 分子量: 376.621
• InChiKey: SYKYUESDKTZQFE-KNPZVZKISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  94.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,3-di-O-acetyl-4,6-dideoxy-α-D-xylo-hexopyranosyl trichloroacetimidate 在 palladium dihydroxide sodium hydroxide 、 4 A molecular sieve 、 Dowex 1 * 8-200 (Cl^- form) 、 氢气 、 potassium carbonate 、 三甲基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， 反应 27.0h， 生成 (2R,3S,4R,5R,6R)-5-Amino-2-aminomethyl-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-((2S,3R,4S,6R)-3,4-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-cyclohexyloxy]-tetrahydro-pyran-3,4-diol; compound with GENERIC INORGANIC NEUTRAL COMPONENT
  参考文献：
  名称：

  Pyranmycins, a Novel Class of Aminoglycosides with Improved Acid Stability:  The SAR of d-Pyranoses on Ring III of Pyranmycin

  摘要：

  The synthesis of a novel class of aminoglycosides, pyranmycins, is reported along with the structure activity relationship (SAR) of their antibacterial activity against Escherichia coli. Two pyranmycins show prominent activity (9 muM). Pyranmycins also manifest superior stability in acidic media. The SAR information will lead to the future designs of pyranmycin against drug resistant bacteria.

  DOI：

  10.1021/ol0269042
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,6R)-2,4-diacetoxy-6-methyl-tetrahydro-pyran-3-yl ester 、 三氯乙腈 在 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 以11%的产率得到2,3-di-O-acetyl-4,6-dideoxy-α-D-xylo-hexopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Pyranmycins, a Novel Class of Aminoglycosides with Improved Acid Stability:  The SAR of d-Pyranoses on Ring III of Pyranmycin

  摘要：

  The synthesis of a novel class of aminoglycosides, pyranmycins, is reported along with the structure activity relationship (SAR) of their antibacterial activity against Escherichia coli. Two pyranmycins show prominent activity (9 muM). Pyranmycins also manifest superior stability in acidic media. The SAR information will lead to the future designs of pyranmycin against drug resistant bacteria.

  DOI：

  10.1021/ol0269042