Acetic acid (2R,3R,5S)-5-((2R,3R,4R,5R)-3,4-diacetoxy-5-azidomethyl-tetrahydro-furan-2-yloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester | 335266-31-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: Acetic acid (2R,3R,5S)-5-((2R,3R,4R,5R)-3,4-diacetoxy-5-azidomethyl-tetrahydro-furan-2-yloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester
• CAS: 335266-31-4
• 化学式: C₂₀H₂₅N₅O₁₁
• 分子量: 511.445
• InChiKey: FEDGHEYWZNMUFD-ZDAYHQPGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.33
• 重原子数：
  36.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  210.21
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,5S)-5-((2R,3R,4R,5R)-3,4-diacetoxy-5-azidomethyl-tetrahydro-furan-2-yloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 在 甲醇 、 sodium methylate 作用下， 反应 18.0h， 生成 1-[(2R,3R,5S)-5-((3R,4S,5R)-5-Azidomethyl-3,4-dihydroxy-tetrahydro-furan-2-yloxymethyl)-3-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione
  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：

  Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-azidomethyl-2-((2S,4R)-4,5-dihydroxy-tetrahydro-furan-2-ylmethoxy)-tetrahydro-furan-3-yl ester 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 Acetic acid (2R,3R,5S)-5-((2R,3R,4R,5R)-3,4-diacetoxy-5-azidomethyl-tetrahydro-furan-2-yloxymethyl)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-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