N-[1-[(2R,3S,5S)-3-azido-5-[[tert-butyl(diphenyl)silyl]oxymethyl]thiolan-2-yl]-2-oxopyrimidin-4-yl]benzamide | 478159-02-3

• 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: N-[1-[(2R,3S,5S)-3-azido-5-[[tert-butyl(diphenyl)silyl]oxymethyl]thiolan-2-yl]-2-oxopyrimidin-4-yl]benzamide
• CAS: 478159-02-3
• 化学式: C₃₂H₃₄N₆O₃SSi
• 分子量: 610.812
• InChiKey: KIILGXCWZXBEAH-GHVWSFOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  43
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[1-[(2R,3S,5S)-3-azido-5-[[tert-butyl(diphenyl)silyl]oxymethyl]thiolan-2-yl]-2-oxopyrimidin-4-yl]benzamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 N-[1-((2R,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：

  Benzoic acid (3R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-thiophen-3-yl ester 在 三氟甲磺酸三甲基硅酯 、 二苯基膦叠氮化物 、 氨 、 间氯过氧苯甲酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 45.0h， 生成 N-[1-[(2R,3S,5S)-3-azido-5-[[tert-butyl(diphenyl)silyl]oxymethyl]thiolan-2-yl]-2-oxopyrimidin-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

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.