3-[(3aR,4R,6R,6aR)-6-((2R,3R,5S)-3-Acetoxy-5-azidomethyl-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 | 335266-39-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 3-[(3aR,4R,6R,6aR)-6-((2R,3R,5S)-3-Acetoxy-5-azidomethyl-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
• CAS: 335266-39-2
• 化学式: C₂₄H₃₃N₅O₁₁
• 分子量: 567.553
• InChiKey: MGMABYRRAPFYLH-COGHNSAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  191.51
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  3-[(3aR,4R,6R,6aR)-6-((2R,3R,5S)-3-Acetoxy-5-azidomethyl-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 在 甲醇 、 水 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 90.0h， 生成 1-[(2R,3R,4S,5R)-5-((2S,3R,5S)-5-Aminomethyl-3-hydroxy-tetrahydro-furan-2-yloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione; compound with trifluoro-acetic acid
  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：

  二碳酸二叔丁酯 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 TEA 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 3-[(3aR,4R,6R,6aR)-6-((2R,3R,5S)-3-Acetoxy-5-azidomethyl-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