Acetic acid (1S,3R,4R,5S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-4-yl ester | 314297-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (1S,3R,4R,5S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-4-yl ester
• 英文别名: [(1S,3R,4R,5S)-1-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(5-methyl-2,4-dioxopyrimidin-1-yl)-6-(2,2,2-trifluoroacetyl)-2-oxa-6-azabicyclo[3.2.0]heptan-4-yl] acetate
• CAS: 314297-02-4
• 化学式: C₃₁H₃₄F₃N₃O₇Si
• 分子量: 645.708
• InChiKey: YCMOZQNCEVAYLG-AQYJNGKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  45
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  115
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Acetic acid (1S,3R,4R,5S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-6-(2,2,2-trifluoro-acetyl)-2-oxa-6-aza-bicyclo[3.2.0]hept-4-yl ester 在 potassium carbonate 、 四丁基氟化铵 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 以28%的产率得到1-[(1S,3R,4R,5S)-4-Hydroxy-1-hydroxymethyl-6-(2,2,2-trifluoro-acetyl)-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：

  Toluene-4-sulfonic acid (3aR,5S,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-(toluene-4-sulfonylamino)-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester 在 4-二甲氨基吡啶 、 戊醇 、 三氟甲磺酸三甲基硅酯 、 sodium 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 硫酸 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 生成 Acetic acid (1S,3R,4R,5S)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-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