(S)-4-Benzyloxycarbonylamino-5-[((3aR,4R,6R,6aR)-2,2-dimethyl-6-purin-9-yl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-methoxy-phosphoryloxy]-pentanoic acid benzyl ester | 212714-87-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: (S)-4-Benzyloxycarbonylamino-5-[((3aR,4R,6R,6aR)-2,2-dimethyl-6-purin-9-yl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-methoxy-phosphoryloxy]-pentanoic acid benzyl ester
• CAS: 212714-87-9
• 化学式: C₃₄H₄₀N₅O₁₁P
• 分子量: 725.692
• InChiKey: BGUDTMKYGBRCQJ-XWXQSVENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  51.0
• 可旋转键数：
  16.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  180.68
• 氢给体数：
  1.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (S)-4-Benzyloxycarbonylamino-5-[((3aR,4R,6R,6aR)-2,2-dimethyl-6-purin-9-yl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-methoxy-phosphoryloxy]-pentanoic acid benzyl ester 在 三氟乙酸 作用下， 反应 0.17h， 以97%的产率得到(S)-4-Benzyloxycarbonylamino-5-[((2R,3S,4R,5R)-3,4-dihydroxy-5-purin-9-yl-tetrahydro-furan-2-ylmethoxy)-methoxy-phosphoryloxy]-pentanoic acid benzyl ester
  参考文献：
  名称：

  Glutamyl Adenylate Analogues Are Inhibitors of Glutamyl-tRNA Synthetase

  摘要：

  Glutamol adenylate 10 was a competitive inhibitor (K-i = 3 pM) of glutamyl-tRNA synthetase from Escherichia coli. The N-6-benzoyl adenine derivative 9 was also an inhibitor (K-i similar to 60 mu M). Replacement of adenine by other bases (purine, cytosine, dihydrocytosine, uridine) resulted in a more than 1000-fold loss in activity, indicating the important contribution of the adenine ring to the enzyme binding. (C) 1998 Academic Press.

  DOI：

  10.1006/bioo.1998.1082
• 作为产物：
  描述：

  2',3'-O-isopropylidenenebularine 在 四氮唑 、 碘 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.2h， 生成 (S)-4-Benzyloxycarbonylamino-5-[((3aR,4R,6R,6aR)-2,2-dimethyl-6-purin-9-yl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethoxy)-methoxy-phosphoryloxy]-pentanoic acid benzyl ester
  参考文献：
  名称：

  Glutamyl Adenylate Analogues Are Inhibitors of Glutamyl-tRNA Synthetase

  摘要：

  Glutamol adenylate 10 was a competitive inhibitor (K-i = 3 pM) of glutamyl-tRNA synthetase from Escherichia coli. The N-6-benzoyl adenine derivative 9 was also an inhibitor (K-i similar to 60 mu M). Replacement of adenine by other bases (purine, cytosine, dihydrocytosine, uridine) resulted in a more than 1000-fold loss in activity, indicating the important contribution of the adenine ring to the enzyme binding. (C) 1998 Academic Press.

  DOI：

  10.1006/bioo.1998.1082