Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[(2R,3S,5R)-3-acetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-5-azidomethyl-tetrahydro-furan-3-yl ester | 335266-27-8

• 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,4R,5R)-4-acetoxy-2-[(2R,3S,5R)-3-acetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-5-azidomethyl-tetrahydro-furan-3-yl ester
• CAS: 335266-27-8
• 化学式: C₂₀H₂₅N₅O₁₁
• 分子量: 511.445
• InChiKey: ZVCMGFMZDXZJBL-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,4R,5R)-4-acetoxy-2-[(2R,3S,5R)-3-acetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-5-azidomethyl-tetrahydro-furan-3-yl ester 在 甲醇 、 水 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 1-[(2R,4S,5R)-5-((2R,3R,4S,5R)-5-Aminomethyl-3,4-dihydroxy-tetrahydro-furan-2-yloxymethyl)-4-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：

  (2S,3R,4R,5R)-5-(azidomethyl)tetrahydrofuran-2,3,4-triyl triacetate 、 3'-O-acetyl-2'-deoxy-5'-O-triphenylmethyluridine 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以49%的产率得到Acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[(2R,3S,5R)-3-acetoxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethoxy]-5-azidomethyl-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