Acetic acid (2S,3R,5S)-3-acetoxy-5-azidomethyl-tetrahydro-furan-2-yl ester | 335266-38-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: Acetic acid (2S,3R,5S)-3-acetoxy-5-azidomethyl-tetrahydro-furan-2-yl ester
• CAS: 335266-38-1
• 化学式: C₉H₁₃N₃O₅
• 分子量: 243.219
• InChiKey: AIYPCVHSKAYRPY-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  110.59
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,5S)-3-acetoxy-5-azidomethyl-tetrahydro-furan-2-yl ester 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 水 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 114.0h， 生成 3-[(3aR,4R,6R,6aR)-6-((2R,3R,5S)-5-Aminomethyl-3-hydroxy-tetrahydro-furan-2-yloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of analogues of the O-β-d-Ribofuranosyl nucleoside moiety of liposidomycins. Part 2: role of the hydroxyl groups upon the inhibition of MraY

  摘要：

  O-beta -D-Ribofuranosyl nucleoside I is the minimal structural entity of liposidomycins that maintains enzyme inhibitory activity on MraY. A set of compounds with hydroxyl patterns different from I has been synthesized. The presence of a hydroxyl group in the 3 " position is essential for the activity. The 3'-deoxy derivative (IV), however, shows a 5-fold improved potency. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00714-9
• 作为产物：
  描述：

  5-azido-3,5-dideoxy-1,2-O-isopropylidene-α-D-ribofuranose 在 吡啶 、 溶剂黄146 作用下， 反应 5.0h， 生成 Acetic acid (2S,3R,5S)-3-acetoxy-5-azidomethyl-tetrahydro-furan-2-yl ester
  参考文献：
  名称：

  Synthesis of analogues of the O-β-d-Ribofuranosyl nucleoside moiety of liposidomycins. Part 2: role of the hydroxyl groups upon the inhibition of MraY

  摘要：

  O-beta -D-Ribofuranosyl nucleoside I is the minimal structural entity of liposidomycins that maintains enzyme inhibitory activity on MraY. A set of compounds with hydroxyl patterns different from I has been synthesized. The presence of a hydroxyl group in the 3 " position is essential for the activity. The 3'-deoxy derivative (IV), however, shows a 5-fold improved potency. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00714-9