Acetic acid (1S,4R,5S)-3-acetoxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-4-yl ester | 314297-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (1S,4R,5S)-3-acetoxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-4-yl ester
• CAS: 314297-21-7
• 化学式: C₂₈H₃₂F₃NO₇Si
• 分子量: 579.645
• InChiKey: AVTKUOLSVQYHNO-SCTDMFTHSA-N

物化性质

• 沸点：
  592.2±50.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  40.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  91.37
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,4R,5S)-3-acetoxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-4-yl ester 在 三氟甲磺酸三甲基硅酯 、 氨 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 1,2-二氯乙烷 为溶剂， 生成 1-((1S,3R,4R,5S)-4-Hydroxy-1-hydroxymethyl-2-oxa-6-aza-bicyclo[3.2.0]hept-3-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of a novel bridged nucleoside bearing a fused-azetidine ring, 3′-amino-3′,4′-BNA monomer

  摘要：

  A novel bridged nucleic acid monomer, 3'-amino-3'-deoxy-5-methyl-3'-N,4'-C-methyleneuridine, was successfully synthesized via a useful and convenient azetidine ring formation under Staudinger's conditions. A H-1 NMR experiment and a PM3 calculation revealed that the sugar moiety of the novel bridged nucleic acid monomer, 3'-amino-3',4'-BNA, was restricted to S-type conformation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01279-6
• 作为产物：
  描述：

  (2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-2-(toluene-4-sulfonyl)-hexahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalene 在 4-二甲氨基吡啶 、 戊醇 、 sodium 作用下， 以 二氯甲烷 、 硫酸 、 溶剂黄146 为溶剂， 生成 Acetic acid (1S,4R,5S)-3-acetoxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-4-yl ester
  参考文献：
  名称：

  Synthesis of a novel bridged nucleoside bearing a fused-azetidine ring, 3′-amino-3′,4′-BNA monomer

  摘要：

  A novel bridged nucleic acid monomer, 3'-amino-3'-deoxy-5-methyl-3'-N,4'-C-methyleneuridine, was successfully synthesized via a useful and convenient azetidine ring formation under Staudinger's conditions. A H-1 NMR experiment and a PM3 calculation revealed that the sugar moiety of the novel bridged nucleic acid monomer, 3'-amino-3',4'-BNA, was restricted to S-type conformation. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01279-6