[3-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-acetic acid benzyl ester | 401515-28-4

• 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: [3-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-acetic acid benzyl ester
• 英文别名: Phenylmethyl 2-{3-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-2,6-dioxo-1,3-dihydropyrimidinyl}acetate；benzyl 2-[3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]acetate
• CAS: 401515-28-4
• 化学式: C₁₉H₂₂N₂O₈
• 分子量: 406.392
• InChiKey: YKZYQSWMHIEZQG-GFOCRRMGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [3-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-acetic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以94%的产率得到[3-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-acetic acid
  参考文献：
  名称：

  Identification of a novel family of nucleosides that specifically inhibit HIV-1 reverse transcriptase

  摘要：

  N-3-Benzyloxycarbonylmethyl- and N-3-carboxymethyl-TBDMS-substituted nucleosides were synthesized and evaluated for activity against HIV replication. It was found that the N-3-carboxymethyl-TBDMS-substituted nucleosides were specific inhibitors of HIV-1 replication. They should be considered as members of a novel and original class of NNRTIs. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00635-7
• 作为产物：
  描述：

  1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine 在 四丁基氟化铵 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 [3-((2R,3R,4S,5R)-3,4-Dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-acetic acid benzyl ester
  参考文献：
  名称：

  Identification of a novel family of nucleosides that specifically inhibit HIV-1 reverse transcriptase

  摘要：

  N-3-Benzyloxycarbonylmethyl- and N-3-carboxymethyl-TBDMS-substituted nucleosides were synthesized and evaluated for activity against HIV replication. It was found that the N-3-carboxymethyl-TBDMS-substituted nucleosides were specific inhibitors of HIV-1 replication. They should be considered as members of a novel and original class of NNRTIs. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00635-7

文献信息

• Identification of a novel family of nucleosides that specifically inhibit HIV-1 reverse transcriptase
  作者：Cristina Chamorro、Esther Lobatón、Marı́a-Cruz Bonache、Erik De Clercq、Jan Balzarini、Sonsoles Velázquez、Ana San-Félix、Marı́a-José Camarasa

  DOI：10.1016/s0960-894x(01)00635-7

  日期：2001.12

  N-3-Benzyloxycarbonylmethyl- and N-3-carboxymethyl-TBDMS-substituted nucleosides were synthesized and evaluated for activity against HIV replication. It was found that the N-3-carboxymethyl-TBDMS-substituted nucleosides were specific inhibitors of HIV-1 replication. They should be considered as members of a novel and original class of NNRTIs. (C) 2001 Elsevier Science Ltd. All rights reserved.