[(3S,5S)-3-azido-5-[[tert-butyl(diphenyl)silyl]oxymethyl]thiolan-2-yl] acetate | 478158-96-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: [(3S,5S)-3-azido-5-[[tert-butyl(diphenyl)silyl]oxymethyl]thiolan-2-yl] acetate
• CAS: 478158-96-2
• 化学式: C₂₃H₂₉N₃O₃SSi
• 分子量: 455.653
• InChiKey: SNHPAOKLHCNOLN-FBIGCWIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  75.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(3S,5S)-3-azido-5-[[tert-butyl(diphenyl)silyl]oxymethyl]thiolan-2-yl] acetate 在 三氟甲磺酸三甲基硅酯 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 13.5h， 生成 N-[1-((2S,3S,5S)-3-Azido-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-benzamide
  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：

  ((2S,4S)-4-Azido-tetrahydro-thiophen-2-ylmethoxy)-tert-butyl-diphenyl-silane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 [(3S,5S)-3-azido-5-[[tert-butyl(diphenyl)silyl]oxymethyl]thiolan-2-yl] acetate
  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