3-azido-1-(4-(methyl-3,5-di-O-benzyl-2-O-methylene-α-D-xylofuranose)-1H-1,2,3-triazol-1-yl)propan-2-ol | 1612222-42-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-azido-1-(4-(methyl-3,5-di-O-benzyl-2-O-methylene-α-D-xylofuranose)-1H-1,2,3-triazol-1-yl)propan-2-ol
• 英文别名: 1-azido-3-[4-[[(2S,3R,4S,5R)-2-methoxy-4-phenylmethoxy-5-(phenylmethoxymethyl)oxolan-3-yl]oxymethyl]triazol-1-yl]propan-2-ol
• CAS: 1612222-42-0
• 化学式: C₂₆H₃₂N₆O₆
• 分子量: 524.577
• InChiKey: VVNIRQULWFCIFA-URQWQUFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3-azido-1-(4-(methyl-3,5-di-O-benzyl-2-O-methylene-α-D-xylofuranose)-1H-1,2,3-triazol-1-yl)propan-2-ol 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.33h， 生成 6-(4-(methyl-3,5-di-O-benzyl-2-O-methylene-α-D-xylofuranose)-1H-1,2,3-triazol-1-yl)-6,7-dihydro-4H-[1,2,3]triazolo[5,1-c][1,4]-oxazine
  参考文献：
  名称：

  Click Chemistry Inspired Synthesis of Morpholine-Fused Triazoles

  摘要：

  The synthesis of triazolyl azido alcohols from terminal alkyne via oxirane ring-opening of epichlorohydrin, followed by click reaction with alkynes, and subsequent azidation of chlorohydroxy triazoles was achieved under a one-pot methodology. The developed triazolyl azido alcohols were further utilized for the synthesis of a diverse range of morpholine-fused triazoles of chemotherapeutic value. The structure of all developed compounds has been elucidated using IR. NMR, MS, and elemental analysis, where four of them have been characterized by single-crystal X-ray analysis.

  DOI：

  10.1021/jo500890w
• 作为产物：
  描述：

  1-O-methyl 3,5-di-O-benzyl α(D)xylo-pentoaldofuranose 在 sodium azide 、 Cu*O₄S^(2-)*5H₂O 、 sodium hydride 、 sodium ascorbate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.33h， 生成 3-azido-1-(4-(methyl-3,5-di-O-benzyl-2-O-methylene-α-D-xylofuranose)-1H-1,2,3-triazol-1-yl)propan-2-ol
  参考文献：
  名称：

  Click Chemistry Inspired Synthesis of Morpholine-Fused Triazoles

  摘要：

  The synthesis of triazolyl azido alcohols from terminal alkyne via oxirane ring-opening of epichlorohydrin, followed by click reaction with alkynes, and subsequent azidation of chlorohydroxy triazoles was achieved under a one-pot methodology. The developed triazolyl azido alcohols were further utilized for the synthesis of a diverse range of morpholine-fused triazoles of chemotherapeutic value. The structure of all developed compounds has been elucidated using IR. NMR, MS, and elemental analysis, where four of them have been characterized by single-crystal X-ray analysis.

  DOI：

  10.1021/jo500890w

文献信息

• Efficient synthesis of ethisterone glycoconjugate via bis-triazole linkage
  作者：Kunj B. Mishra、Bhuwan B. Mishra、Vinod K. Tiwari

  DOI：10.1016/j.carres.2014.09.001

  日期：2014.11

  Synthesis of sugar based triazolyl azido-alcohols was accomplished via one pot click reaction of glycosyl alkynes with epichlorohydrin in aqueous medium. All the developed triazolyl azido-alcohols were further utilized for the synthesis of bis-triazolyl ethisterone glycoconjugates using CuAAC reaction. The developed triazole-linked ethisterone glycoconjugates would be crucial in androgen receptor pharmacology and chemical biology. (C) 2014 Elsevier Ltd. All rights reserved.