3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-methoxybenzonitrile | 1038412-66-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-methoxybenzonitrile
• CAS: 1038412-66-6
• 化学式: C₁₃H₁₅NO₅
• 分子量: 265.266
• InChiKey: UZYRLZREIVGITM-LPWJVIDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2R,3R,4S,5S)-2-(acetoxymethyl)-5-(5-cyano-2-methoxyphenyl)tetrahydrofuran-3,4-diyl diacetate 在 氨 作用下， 以 甲醇 为溶剂， 以92%的产率得到3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-methoxybenzonitrile
  参考文献：
  名称：

  Friedel–Crafts and modified Vorbrüggen ribosylation. A short synthesis of aryl and heteroaryl-C-nucleosides

  摘要：

  A direct coupling of aryl donor and tetra-O-acetylribose in the presence of Lewis acid led to beta-C-nucleosides in good yields. In contrast, for deactivated electron-poor aromatics, a modified Vorbruggen ribosylation reaction was investigated and successfully applied in the case of 2-trimethylsilyl-thiazole. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.04.105

文献信息

• Friedel–Crafts and modified Vorbrüggen ribosylation. A short synthesis of aryl and heteroaryl-C-nucleosides
  作者：Marie Spadafora、Mohamed Mehiri、Alain Burger、Rachid Benhida

  DOI：10.1016/j.tetlet.2008.04.105

  日期：2008.6

  A direct coupling of aryl donor and tetra-O-acetylribose in the presence of Lewis acid led to beta-C-nucleosides in good yields. In contrast, for deactivated electron-poor aromatics, a modified Vorbruggen ribosylation reaction was investigated and successfully applied in the case of 2-trimethylsilyl-thiazole. (C) 2008 Elsevier Ltd. All rights reserved.