Acetic acid 6-bromo-2-((2R,4R,5S,6R)-4,5-diacetoxy-6-azidomethyl-tetrahydro-pyran-2-yl)-5,8-dioxo-5,8-dihydro-naphthalen-1-yl ester | 870075-92-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: Acetic acid 6-bromo-2-((2R,4R,5S,6R)-4,5-diacetoxy-6-azidomethyl-tetrahydro-pyran-2-yl)-5,8-dioxo-5,8-dihydro-naphthalen-1-yl ester
• 英文别名: [(2R,3S,4R,6R)-3-acetyloxy-6-(1-acetyloxy-6-bromo-5,8-dioxonaphthalen-2-yl)-2-(azidomethyl)oxan-4-yl] acetate
• CAS: 870075-92-6
• 化学式: C₂₂H₂₀BrN₃O₉
• 分子量: 550.319
• InChiKey: FZEIOSAERLBJEL-IDVKNYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  137
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Acetic acid 6-bromo-2-((2R,4R,5S,6R)-4,5-diacetoxy-6-azidomethyl-tetrahydro-pyran-2-yl)-5,8-dioxo-5,8-dihydro-naphthalen-1-yl ester 在 ammonium acetate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 67.0h， 生成 Acetic acid (2R,3S,4R,6R)-3-acetoxy-2-azidomethyl-6-(11-hydroxy-1,7,12-trioxo-1,2,3,4,7,12-hexahydro-benzo[j]phenanthridin-10-yl)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of 5-aza-analogues of angucyclines: manipulation of the 2-deoxy-C-glycoside subunit

  摘要：

  Based on a heterocyclic Diels-Alder strategy, a concise synthesis of 5-aza-analogues of angucyclines bearing a 2-deoxy-C-glycoside subunit is reported. Starting from a common intermediate, a peracetylated D-2-deoxyglucose could be linked to carbons C9 or C10 of the tetracyclic framework. Further manipulations of the sugar residue allowed the installation of bromo and azido substituents at carbon C6'. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.053
• 作为产物：
  描述：

  Acetic acid 5-acetoxy-2-((2R,4R,5S,6R)-4,5-diacetoxy-6-azidomethyl-tetrahydro-pyran-2-yl)-naphthalen-1-yl ester 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 反应 3.0h， 以38%的产率得到Acetic acid 6-bromo-2-((2R,4R,5S,6R)-4,5-diacetoxy-6-azidomethyl-tetrahydro-pyran-2-yl)-5,8-dioxo-5,8-dihydro-naphthalen-1-yl ester
  参考文献：
  名称：

  Synthesis of 5-aza-analogues of angucyclines: manipulation of the 2-deoxy-C-glycoside subunit

  摘要：

  Based on a heterocyclic Diels-Alder strategy, a concise synthesis of 5-aza-analogues of angucyclines bearing a 2-deoxy-C-glycoside subunit is reported. Starting from a common intermediate, a peracetylated D-2-deoxyglucose could be linked to carbons C9 or C10 of the tetracyclic framework. Further manipulations of the sugar residue allowed the installation of bromo and azido substituents at carbon C6'. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.053