(1S,3R,4R,5S)-4-Acetoxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-oxa-6-aza-bicyclo[3.2.0]heptane-6-carboxylic acid benzyl ester | 314297-03-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4R,5S)-4-Acetoxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-oxa-6-aza-bicyclo[3.2.0]heptane-6-carboxylic acid benzyl ester
• 英文别名: benzyl (1S,3R,4R,5S)-4-acetyloxy-1-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(5-methyl-2,4-dioxopyrimidin-1-yl)-2-oxa-6-azabicyclo[3.2.0]heptane-6-carboxylate
• CAS: 314297-03-5
• 化学式: C₃₇H₄₁N₃O₈Si
• 分子量: 683.833
• InChiKey: UAYYFLXTFOERAV-MHHBZGPPSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,5S)-4-Acetoxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-oxa-6-aza-bicyclo[3.2.0]heptane-6-carboxylic acid benzyl ester 在 potassium carbonate 、 四丁基氟化铵 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 以86%的产率得到(1S,3R,4R,5S)-4-Hydroxy-1-hydroxymethyl-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-oxa-6-aza-bicyclo[3.2.0]heptane-6-carboxylic acid benzyl 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
• 作为产物：
  描述：

  (2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-hexahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalene 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 、 硫酸 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 生成 (1S,3R,4R,5S)-4-Acetoxy-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-oxa-6-aza-bicyclo[3.2.0]heptane-6-carboxylic acid benzyl 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