(2S,3S,5R)-3-benzoyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carboxylic acid | 154230-41-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,5R)-3-benzoyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carboxylic acid
• 英文别名: (2S,3S,5R)-3-benzoyloxy-5-[5-methyl-2,4-dioxo-3-(phenylmethoxymethyl)pyrimidin-1-yl]oxolane-2-carboxylic acid
• CAS: 154230-41-8
• 化学式: C₂₅H₂₄N₂O₈
• 分子量: 480.474
• InChiKey: ZFMQUGPYZSPOJW-HBMCJLEFSA-N

物化性质

• 沸点：
  658.4±65.0 °C(predicted)
• 密度：
  1.43±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3S,5R)-3-benzoyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carboxylic acid 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(2S,3S,5R)-2-(2-hydroxyethoxy)-5-[5-methyl-2,4-dioxo-3-(phenylmethoxymethyl)pyrimidin-1-yl]oxolan-3-yl] benzoate
  参考文献：
  名称：

  Nucleic Acid Mimics. Synthesis of Ethylene Glycol- and Propoxy- Linked Thymidyl-Tetrahydrofuranylthymine Dimers via a Vorbruggen-type Glycosylation Reaction

  摘要：

  Two thymidyl-tetrahydrofuranylthymine dimers, 15 and 16, were synthesized stereospecifically in good yield via a Vorbruggen-type reaction between glycol ether 4 or propoxy alcohol 7 and acetate 12.

  DOI：

  10.1021/jo00081a003
• 作为产物：
  描述：

  5'-O-tert-butyldiphenylsilylthymidine 在 吡啶 、 chromium(VI) oxide 、 乙酸酐 、 氟化氢吡啶 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,3S,5R)-3-benzoyloxy-5-(3-benzyloxymethyl-5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-carboxylic acid
  参考文献：
  名称：

  Nucleic Acid Mimics. Synthesis of Ethylene Glycol- and Propoxy- Linked Thymidyl-Tetrahydrofuranylthymine Dimers via a Vorbruggen-type Glycosylation Reaction

  摘要：

  Two thymidyl-tetrahydrofuranylthymine dimers, 15 and 16, were synthesized stereospecifically in good yield via a Vorbruggen-type reaction between glycol ether 4 or propoxy alcohol 7 and acetate 12.

  DOI：

  10.1021/jo00081a003

文献信息

• Synthesis, anti-HIV activity, and resistance profile of thymidine phosphonomethoxy nucleosides and their bis-isopropyloxymethylcarbonyl (bisPOC) prodrugs
  作者：Richard L. Mackman、Lijun Zhang、Vidya Prasad、Constantine G. Boojamra、Janet Douglas、Deborah Grant、Hon Hui、Choung U. Kim、Genevieve Laflamme、Jay Parrish、Antitsa D. Stoycheva、Swami Swaminathan、KeYu Wang、Tomas Cihlar

  DOI：10.1016/j.bmc.2007.05.047

  日期：2007.8

  (NRTIs), 3'-azido-2',3'-dideoxythymidine (AZT), 2',3'-didehydro-2',3'-dideoxythymidine (d4T), and 2',3'-dideoxythymidine (ddT), were synthesized. The anti-HIV activity against wild-type and several major nucleoside-resistant strains of HIV-1 was evaluated together with the inhibition of wild-type HIV reverse transcriptase (RT). Phosphonomethoxy analog of d4T, 8 (d4TP), demonstrated antiviral activity with

  含胸腺嘧啶核苷逆转录酶抑制剂（NRTIs），3'-叠氮基2'，3'-二脱氧胸苷（AZT），2'，3'-二脱氢-2'，3'-二脱氧胸苷（d4T）的膦甲氧基核苷类似物，合成2'，3'-二脱氧胸苷（ddT）。与野生型HIV逆转录酶（RT）的抑制作用一起评估了抗HIV-1对野生型和几种主要的抗核苷主要毒株的抗HIV活性。d4T，8（d4TP）的膦氧甲氧基类似物表现出抗病毒活性，其EC（50）值为26 microM，而ddT，7（ddTP）和AZT，6（AZTP）的膦酰甲氧基类似物在浓度升高时均无活性到200 microM。双异丙氧基甲氧羰基（bisPOC）前药分别将7和8的抗HIV活性提高了150倍和29倍，从而确定抗病毒耐药性。与bisPOC PMPA（替诺福韦DF）1相比，K65R RT突变病毒对bisPOC前药7和8的耐药性更高。但是，bisPOC前药7对含有多个胸苷类似物突变（6TAMs）
• Synthesis And Anti-Hiv Activity Of Cyclic Pyrimidine Phosphonomethoxy Nucleosides And Their Prodrugs: A Comparison Of Phosphonates And Corresponding Nucleosides
  作者：Richard L. Mackman、Lijun Zhang、Vidya Prasad、Constantine G. Boojamra、James Chen、Janet Douglas、Deborah Grant、Genevieve Laflamme、Hon Hui、Choung U. Kim、Jay Parrish、Antitsa D. Stoycheva、Swami Swaminathan、KeYu Wang、Tomas Cihlar

  DOI：10.1080/15257770701490126

  日期：2007.11.26

  Cyclic phosphonomethoxy pyrimidine nucleosides that are bioisosteres of the monophosphate metabolites of HIV reverse transcriptase (RT) inhibitors AZT, d4T, and ddC have been synthesized. The RT inhibitory activities of the phosphonates were reduced for both dideoxy (dd) and dideoxydide-hydro (d4) analogs compared to the nucleosides. Bis-isopropyloxymethylcarbanyl (BisPOC) prodrugs were prepared on selected compounds and provided > 150-fold improvements in antiviral activity.
• Nucleic Acid Mimics. Synthesis of Ethylene Glycol- and Propoxy- Linked Thymidyl-Tetrahydrofuranylthymine Dimers via a Vorbruggen-type Glycosylation Reaction
  作者：Kelly Teng、P. Dan Cook

  DOI：10.1021/jo00081a003

  日期：1994.1

  Two thymidyl-tetrahydrofuranylthymine dimers, 15 and 16, were synthesized stereospecifically in good yield via a Vorbruggen-type reaction between glycol ether 4 or propoxy alcohol 7 and acetate 12.