(2R,3S,6S)-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol | 1366497-60-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (2R,3S,6S)-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol
• 英文别名: (2R,3S,6S)-6-(1-benzyltriazol-4-yl)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol
• CAS: 1366497-60-0
• 化学式: C₁₅H₁₇N₃O₃
• 分子量: 287.318
• InChiKey: NNHQQOVXKMYGAB-SOUVJXGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S,6S)-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol 在 吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 (2S,3S,6S)-6-(1-phenyl-1H-1,2,3-triazol-4-yl)-2-(phenylselanylmethyl)-3,6-dihydro-2H-pyran-3-ol
  参考文献：
  名称：

  Synthesis of 1,2,3-triazolylpyranosides through click chemistry reaction

  摘要：

  We have developed an efficient method for the synthesis of functionalized C-glycosyl 1,2,3-triazoles through a Cu(1)-promoted azide-alkyne 1,3-dipolar cycloaddition between a TMS-protected C-alkynyl-glycoside and organic azides. The reaction was accelerated by ultrasound irradiation and the addition of a base was not necessary to obtain the 1,2,3-triazole product. Moreover, further manipulation of the products led to chiral molecules with a C-glycoside linkage. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.102
• 作为产物：
  描述：

  ((2R,3S,6S)-3-acetoxy-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate 在 水 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 以94%的产率得到(2R,3S,6S)-6-(1-benzyl-1H-1,2,3-triazol-4-yl)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol
  参考文献：
  名称：

  Synthesis of 1,2,3-triazolylpyranosides through click chemistry reaction

  摘要：

  We have developed an efficient method for the synthesis of functionalized C-glycosyl 1,2,3-triazoles through a Cu(1)-promoted azide-alkyne 1,3-dipolar cycloaddition between a TMS-protected C-alkynyl-glycoside and organic azides. The reaction was accelerated by ultrasound irradiation and the addition of a base was not necessary to obtain the 1,2,3-triazole product. Moreover, further manipulation of the products led to chiral molecules with a C-glycoside linkage. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.102

文献信息

• Synthesis of 1,2,3-triazolylpyranosides through click chemistry reaction
  作者：Hélio A. Stefani、Nathália C.S. Silva、Flávia Manarin、Diogo S. Lüdtke、Julio Zukerman-Schpector、Lucas Sousa Madureira、Edward R.T. Tiekink

  DOI：10.1016/j.tetlet.2012.01.102

  日期：2012.4

  We have developed an efficient method for the synthesis of functionalized C-glycosyl 1,2,3-triazoles through a Cu(1)-promoted azide-alkyne 1,3-dipolar cycloaddition between a TMS-protected C-alkynyl-glycoside and organic azides. The reaction was accelerated by ultrasound irradiation and the addition of a base was not necessary to obtain the 1,2,3-triazole product. Moreover, further manipulation of the products led to chiral molecules with a C-glycoside linkage. (C) 2012 Elsevier Ltd. All rights reserved.