3,4,6-tri-O-benzoyl-2-deoxy-2-bromo-α-D-talopyranosylazide | 1338812-04-6

• 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: 3,4,6-tri-O-benzoyl-2-deoxy-2-bromo-α-D-talopyranosylazide
• 英文别名: [(2R,3S,4S,5S,6S)-6-azido-3,4-dibenzoyloxy-5-bromooxan-2-yl]methyl benzoate
• CAS: 1338812-04-6
• 化学式: C₂₇H₂₂BrN₃O₇
• 分子量: 580.392
• InChiKey: VKRHXNUVIFWGII-BAHGYDIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  三-O-苯甲酰基-D-半乳糖烯 在 N-溴代丁二酰亚胺(NBS) 、 叠氮基三甲基硅烷 作用下， 以 乙腈 为溶剂， 反应 0.07h， 生成 3,4,6-tri-O-benzoyl-2-deoxy-2-bromo-α-D-talopyranosylazide 、 3,4,6-tri-O-benzoyl-2-deoxy-2-bromo-α-D-galactopyranosylazide
  参考文献：
  名称：

  Stereoselective Conversion of Dihydropyran and Glycals to 1-Azido-2-halo Derivatives Using NIS/NBS-TMSN₃

  摘要：

  Dihydropyran and glycals are readily converted to the corresponding trans-2-deoxy-2-haloazide derivatives in excellent yields within a few minutes using NIS/NBS-TMSN3 at rt in the absence of any catalyst. The use of stoichiometric amounts of the reagents under mild experimental conditions together with the simplicity of the reaction protocol is the notable feature of this transformation.

  DOI：

  10.1080/07328303.2011.590259

文献信息

• Stereoselective Conversion of Dihydropyran and Glycals to 1-Azido-2-halo Derivatives Using NIS/NBS-TMSN₃
  作者：Syed Khalid Yousuf、Altaf Hussain、Deepak Kumar Sharma、Abdul Haleem Wani、Baldev Singh、Debaraj Mukherjee、Subhash C. Taneja

  DOI：10.1080/07328303.2011.590259

  日期：2011.2.1

  Dihydropyran and glycals are readily converted to the corresponding trans-2-deoxy-2-haloazide derivatives in excellent yields within a few minutes using NIS/NBS-TMSN3 at rt in the absence of any catalyst. The use of stoichiometric amounts of the reagents under mild experimental conditions together with the simplicity of the reaction protocol is the notable feature of this transformation.