[(2S,4S,5R)-4-azido-5-(6-chloropurin-9-yl)thiolan-2-yl]methanol | 478159-07-8

• 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-(6-chloropurin-9-yl)thiolan-2-yl]methanol
• CAS: 478159-07-8
• 化学式: C₁₀H₁₀ClN₇OS
• 分子量: 311.755
• InChiKey: NWBOSDXEMSFRBL-JFWOZONXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(2S,4S,5R)-4-azido-5-(6-chloropurin-9-yl)thiolan-2-yl]methanol 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以51%的产率得到[5-(6-Amino-purin-9-yl)-4-azido-tetrahydro-thiophen-2-yl]-methanol
  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：

  6-chloro-9-trimethylsilylpurine 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 16.0h， 生成 [(2S,4S,5R)-4-azido-5-(6-chloropurin-9-yl)thiolan-2-yl]methanol
  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.