8,9-anhydro-N-demethylerythromycin A 2',3'-carbamate-11,12-carbonate-6,9-hemiketal | 1166834-90-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8,9-anhydro-N-demethylerythromycin A 2',3'-carbamate-11,12-carbonate-6,9-hemiketal
• 英文别名: (2R,3R,7R,8R,11R,12S,13S,14R,15R)-14-[[(3aR,4S,6R,7aS)-1,6-dimethyl-2-oxo-4,6,7,7a-tetrahydro-3aH-pyrano[4,3-d][1,3]oxazol-4-yl]oxy]-8-ethyl-12-[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-2,7,11,13,15,17-hexamethyl-4,6,9,18-tetraoxatricyclo[13.2.1.03,7]octadec-1(17)-ene-5,10-dione
• CAS: 1166834-90-7
• 化学式: C₃₈H₅₉NO₁₄
• 分子量: 753.885
• InChiKey: HRPGRJNEQDVKRY-VPFAZEEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  53
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  167
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  8,9-anhydro-N-demethylerythromycin A 2',3'-carbamate-11,12-carbonate-6,9-hemiketal 在 Selectfluor 作用下， 以 水 、 乙腈 为溶剂， 反应 0.67h， 以80%的产率得到N-demethylflurithromycin A 2',3'-carbamate-11,12-carbonate-6,9-hemiketal
  参考文献：
  名称：

  Synthesis of 8-Fluorinated Erythromycin Cyclic 2′,3′-Carbamates

  摘要：

  Methodology is described for the preparation of a 2',3'-carbamate-11,12-carbonate analog of flurithromycin and its 3-O-descladinosylflurithromycin analog from (9E)-erythromycin A 9-oxime. Phosgene was used for the carbonylation reactions. SelectfluorTM was an effective fluorinating agent of the intermediate 8,9-anhydro-N-demethylerythromycin A 2',3'-carbamate-11,12-carbonate-6,9-hemiketal under mild aqueous conditions.

  DOI：

  10.1080/00397910802618455
• 作为产物：
  描述：

  (9E)-N'-demethylerythromycin A 9-oxime 2',3'-carbamate-11,12-carbonate 在 pyridinium chlorochromate 、 水 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以63%的产率得到8,9-anhydro-N-demethylerythromycin A 2',3'-carbamate-11,12-carbonate-6,9-hemiketal
  参考文献：
  名称：

  Synthesis of 8-Fluorinated Erythromycin Cyclic 2′,3′-Carbamates

  摘要：

  Methodology is described for the preparation of a 2',3'-carbamate-11,12-carbonate analog of flurithromycin and its 3-O-descladinosylflurithromycin analog from (9E)-erythromycin A 9-oxime. Phosgene was used for the carbonylation reactions. SelectfluorTM was an effective fluorinating agent of the intermediate 8,9-anhydro-N-demethylerythromycin A 2',3'-carbamate-11,12-carbonate-6,9-hemiketal under mild aqueous conditions.

  DOI：

  10.1080/00397910802618455

文献信息

• Synthesis of 8-Fluorinated Erythromycin Cyclic 2′,3′-Carbamates
  作者：Audun Heggelund、Kjell Undheim

  DOI：10.1080/00397910802618455

  日期：2009.5.7

  Methodology is described for the preparation of a 2',3'-carbamate-11,12-carbonate analog of flurithromycin and its 3-O-descladinosylflurithromycin analog from (9E)-erythromycin A 9-oxime. Phosgene was used for the carbonylation reactions. SelectfluorTM was an effective fluorinating agent of the intermediate 8,9-anhydro-N-demethylerythromycin A 2',3'-carbamate-11,12-carbonate-6,9-hemiketal under mild aqueous conditions.