(2S,3R,4S,5S)-4-acetoxy-2-((benzoyloxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate | 154463-67-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: (2S,3R,4S,5S)-4-acetoxy-2-((benzoyloxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate
• 英文别名: 1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylo-furanosyl)thymine；Bz(-3)[Bz(-5)]L-Xylf2Ac(b)-thymin-1-yl；[(2S,3R,4S,5S)-4-acetyloxy-3-benzoyloxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• CAS: 154463-67-9
• 化学式: C₂₆H₂₄N₂O₉
• 分子量: 508.485
• InChiKey: DARPMTHTYISXJU-KGSLCBSSSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5S)-4-acetoxy-2-((benzoyloxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三(三甲基硅基)硅烷 、 二苯基磷酸 、 氨 、 一水合肼 、 溶剂黄146 、 三苯基膦 、 硫代氯甲酸苯酯 、 偶氮二甲酸二乙酯 作用下， 以 吡啶 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 stavudine
  参考文献：
  名称：

  New Unnatural L-Nucleoside Enantiomers:From Their Stereospecific Synthesis to Their Biological Activities

  摘要：

  Several purine and pyrimidine beta-L-dideoxynucleosides were stereospecifically synthesized and their antiviral properties examined. Two of them, namely beta-L-2', 3'-dideoxyadenosine (beta-L-ddA) and its 2',3'-didehydro derivative (beta-L-d4A) were found to have significant anti-human immunodeficiency virus (HIV) and anti-hepatitis B virus (HBV) activities in cell culture.

  DOI：

  10.1080/07328319708006190
• 作为产物：
  描述：

  胸腺嘧啶 在 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3R,4S,5S)-4-acetoxy-2-((benzoyloxy)methyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl benzoate
  参考文献：
  名称：

  New Unnatural L-Nucleoside Enantiomers:From Their Stereospecific Synthesis to Their Biological Activities

  摘要：

  Several purine and pyrimidine beta-L-dideoxynucleosides were stereospecifically synthesized and their antiviral properties examined. Two of them, namely beta-L-2', 3'-dideoxyadenosine (beta-L-ddA) and its 2',3'-didehydro derivative (beta-L-d4A) were found to have significant anti-human immunodeficiency virus (HIV) and anti-hepatitis B virus (HBV) activities in cell culture.

  DOI：

  10.1080/07328319708006190

文献信息

• Synthesis and antiviral evaluation of β-L-<i>Xylo</i>-fuanosyl nucleosides of the five naturally occurring nucleic acid bases
  作者：Gilles Gosselin、Marie-Christine Bergogne、Jean-Louis Imbach

  DOI：10.1002/jhet.5570300510

  日期：1993.10

  The β-L-xylo-furanosyl analogues of the naturally occurring nucleosides have been synthesized and their antiviral properties examined. All these compounds were hitherto unknown and they were stereospecifically prepared by glycosylation of pyrimidine and purine aglycons with a suitably peracyl-L-xylo-furanose (specially synthesized from L-xylose for our present purpose), followed by removal of the protecting

  已经合成了天然存在的核苷的β-L-二甲苯基-呋喃糖基类似物，并研究了它们的抗病毒特性。迄今为止，所有这些化合物都是未知的，它们是通过嘧啶和嘌呤糖苷配基与合适的过酰基-L-木糖-呋喃糖（为达到我们目前的目的特别从L-木糖合成）进行糖基化立体定向制备的，然后除去保护基团。测试了所有制备的化合物对多种DNA和RNA病毒（包括HIV）的活性，但它们未显示出显着的抗病毒活性。
• HALO-DEHYDRO-3'-DEOXYURACIL PHOSPHORAMIDATES AND RELATED COMPOUNDS AND THEIR USE IN TREATING MEDICAL CONDITIONS
  申请人：[en]ROME THERAPEUTICS, INC.

  公开号：WO2024107850A1

  公开（公告）日：2024-05-23

  Substituted halo-dehydro-3'-deoxyuracil phosphoramidates and related compounds, pharmaceutical compositions, their use for inhibiting LINE1 reverse transcriptase and/or HERV-K reverse transcriptase activity, and their use in the treatment of medical disorders, such as cancer, are disclosed herein.