[(2S,4S,5R)-4-azido-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)thiolan-2-yl]methyl benzoate | 478158-98-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: [(2S,4S,5R)-4-azido-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)thiolan-2-yl]methyl benzoate
• CAS: 478158-98-4
• 化学式: C₂₄H₂₁N₅O₅S
• 分子量: 491.527
• InChiKey: HYFGCYGPCHDNMJ-CNNODRBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(2S,4S,5R)-4-azido-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)thiolan-2-yl]methyl benzoate 在 甲醇 、 sodium methylate 作用下， 反应 15.0h， 以57%的产率得到1-(3-Azido-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel d-2′-Azido-2′,3′-dideoxyarabinofuranosyl-4′-thiopyrimidines and purines

  摘要：

  Novel D-2'-azido-2',3-dideoxyarabinofuranosyl-4'-thiopyrimidines and purines have been synthesized, starting from L-xylose via azidation at the T-position as a key step. Most of the final nucleosides exhibited toxicity-dependent anti-HIV-1 activity, among which D-alpha-adenine analogue 3h was found to be the most cytotoxic. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00394-3
• 作为产物：
  描述：

  O,O-二(三甲基甲硅烷基)胸苷 在 吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 49.5h， 生成 [(2S,4S,5R)-4-azido-5-(3-benzoyl-5-methyl-2,4-dioxopyrimidin-1-yl)thiolan-2-yl]methyl benzoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Novel d-2′-Azido-2′,3′-dideoxyarabinofuranosyl-4′-thiopyrimidines and purines

  摘要：

  Novel D-2'-azido-2',3-dideoxyarabinofuranosyl-4'-thiopyrimidines and purines have been synthesized, starting from L-xylose via azidation at the T-position as a key step. Most of the final nucleosides exhibited toxicity-dependent anti-HIV-1 activity, among which D-alpha-adenine analogue 3h was found to be the most cytotoxic. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00394-3

文献信息

• Synthesis and Biological Evaluation of Novel d-2′-Azido-2′,3′-dideoxyarabinofuranosyl-4′-thiopyrimidines and purines
  作者：Hea Ok Kim、Yong Hee Park、Hyung Ryong Moon、Lak Shin Jeong

  DOI：10.1016/s0960-894x(02)00394-3

  日期：2002.9

  Novel D-2'-azido-2',3-dideoxyarabinofuranosyl-4'-thiopyrimidines and purines have been synthesized, starting from L-xylose via azidation at the T-position as a key step. Most of the final nucleosides exhibited toxicity-dependent anti-HIV-1 activity, among which D-alpha-adenine analogue 3h was found to be the most cytotoxic. (C) 2002 Elsevier Science Ltd. All rights reserved.