{3-[(2R,3R,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl}-acetic acid benzyl ester | 401515-18-2

• 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,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl}-acetic acid benzyl ester
• 英文别名: benzyl 2-[3-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxy-tetrahydrofuran-2-yl]-5-methyl-2,6-dioxo-pyrimidin-1-yl]acetate；benzyl 2-[3-[(2R,3R,4R,5R)-3-[tert-butyl(dimethyl)silyl]oxy-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-hydroxyoxolan-2-yl]-5-methyl-2,6-dioxopyrimidin-1-yl]acetate
• CAS: 401515-18-2
• 化学式: C₃₁H₅₀N₂O₈Si₂
• 分子量: 634.918
• InChiKey: GJLXPBUYTOEBFF-GTVIQNQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  {3-[(2R,3R,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl}-acetic acid benzyl ester 在 N,N'-硫羰基二咪唑 、 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile 、 三正丁基氢锡 作用下， 以 甲苯 、 乙腈 为溶剂， 以59%的产率得到{3-[(2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-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
• 作为产物：
  描述：

  1-[2',5'-bis-O-(tert-butyldimethylsilyl)-β-D-ribofuranosyl]thymine 、 2-溴乙酸苄酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以90%的产率得到{3-[(2R,3R,4R,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-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.