[(1R,2R,3S,4R,5R)-3,4-dibenzoyloxy-8-oxa-6-azabicyclo[3.2.1]octan-2-yl] benzoate | 225663-05-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1R,2R,3S,4R,5R)-3,4-dibenzoyloxy-8-oxa-6-azabicyclo[3.2.1]octan-2-yl] benzoate
• CAS: 225663-05-8
• 化学式: C₂₇H₂₃NO₇
• 分子量: 473.482
• InChiKey: OZKRTSWARUHVIU-GNADVCDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(1R,2R,3S,4R,5R)-3,4-dibenzoyloxy-8-oxa-6-azabicyclo[3.2.1]octan-2-yl] benzoate 在 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 以98%的产率得到3S,4R,6R-3,4,5-tribenzoyloxy-6-hydroxyazepan
  参考文献：
  名称：

  Efficient synthesis of seven-membered iminocyclitols from glycosylenamines

  摘要：

  Seven membered iminocyclitols are synthesized in four steps from easily available glycosylenamines (D-gluco, D-galacto, and D-manno configurations) through 1,6-aza-anhydrosugar derivatives. These intermediates are transformed into 2-hydroxy- and 2-unsubstituted azepanes depending on the reactants used for the cleavage of the C1-O bond. The overall yields are high. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00649-8
• 作为产物：
  描述：

  1,6-anhydro-2,3,4-tri-O-benzoyl-N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine 在 氯 作用下， 以 二氯甲烷 为溶剂， 生成 [(1R,2R,3S,4R,5R)-3,4-dibenzoyloxy-8-oxa-6-azabicyclo[3.2.1]octan-2-yl] benzoate
  参考文献：
  名称：

  Efficient synthesis of seven-membered iminocyclitols from glycosylenamines

  摘要：

  Seven membered iminocyclitols are synthesized in four steps from easily available glycosylenamines (D-gluco, D-galacto, and D-manno configurations) through 1,6-aza-anhydrosugar derivatives. These intermediates are transformed into 2-hydroxy- and 2-unsubstituted azepanes depending on the reactants used for the cleavage of the C1-O bond. The overall yields are high. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00649-8

文献信息

• Synthesis of seven-membered iminosugars fused thiazolidin-4-one and benzthiazinan-4-one and their HIV-RT inhibitory activity
  作者：Yuheng Hou、Shunkai Xing、Jie Shao、Zhuqing Yin、Le Hao、Tianyu Yang、Hongzhi Zhang、Mo Zhu、Hua Chen、Xiaoliu Li

  DOI：10.1016/j.carres.2016.02.011

  日期：2016.6

  Novel seven-membered iminosugars fused thiazolidin-4-one and benzthiazinan-4-one were conveniently synthesized by the tandem Staudinger/aza-Wittig/cyclization reaction under microwave radiation. Benzoyl group (Bz) migrations were found in the synthesis of 8c and 9b using D-galactoside or D-mannoside as starting materials, respectively, which was suggested by HMBC and X-ray. The new bi/tricyclic iminosugars

  通过串联的Staudinger / aza-Wittig /环化反应在微波辐射下方便地合成了融合了噻唑烷丁-4-酮和苯并噻嗪南-4-酮的新型七元亚氨基糖。HMBC和X射线表明，分别以D-半乳糖苷或D-甘露糖苷为原料，在8c和9b的合成中发现了苯甲酰基（Bz）迁移。检查了新的双/三环亚氨基糖3〜4（ad）和5（bd）的HIV逆转录酶（RT）抑制活性。结果表明，除5b外的所有化合物均可有效抑制RT活性。其中，化合物3c和4c是最好的化合物，其RT抑制活性的IC50值分别为2.11 microM和2.73 microM。