((2R,3S,6S)-3-hydroxy-6-(1-phenyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl methanesulfonate | 1366497-74-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ((2R,3S,6S)-3-hydroxy-6-(1-phenyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl methanesulfonate
• CAS: 1366497-74-6
• 化学式: C₁₅H₁₇N₃O₅S
• 分子量: 351.383
• InChiKey: JGDIGJCJMNXACJ-SOUVJXGZSA-N

物化性质

• 沸点：
  634.7±65.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103.54
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  二苯基二硒醚 、 ((2R,3S,6S)-3-hydroxy-6-(1-phenyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl methanesulfonate 在 sodium tetrahydroborate 作用下， 以 乙醇 、 四氢呋喃 为溶剂， 反应 24.0h， 以77%的产率得到(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：

  1-(4,6-di-O-acetyl-2,3-dideoxy-D-erythro-hex-2-enopyranosyl)-2-trimethylsilylacetylene 在 吡啶 、 copper(l) iodide 、 四丁基氟化铵 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 ((2R,3S,6S)-3-hydroxy-6-(1-phenyl-1H-1,2,3-triazol-4-yl)-3,6-dihydro-2H-pyran-2-yl)methyl methanesulfonate
  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