(S)-2-Benzyloxycarbonylamino-4-[3-((2R,3R,3aS,9aR)-3-hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-butyric acid benzyl ester | 162825-80-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: (S)-2-Benzyloxycarbonylamino-4-[3-((2R,3R,3aS,9aR)-3-hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-butyric acid benzyl ester
• CAS: 162825-80-1
• 化学式: C₄₀H₅₇N₃O₁₁Si₂
• 分子量: 812.077
• InChiKey: RXLMLAKZLKCRSQ-BHQPXCIASA-N

物化性质

• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  56.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  165.78
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (S)-2-Benzyloxycarbonylamino-4-[3-((2R,3R,3aS,9aR)-3-hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-butyric acid benzyl ester 在 对甲苯磺酸 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 (S)-2-Benzyloxycarbonylamino-4-{3-[(2R,3R,4R,5R)-4-hydroxy-5-hydroxymethyl-3-(tetrahydro-pyran-2-yloxy)-tetrahydro-furan-2-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl}-butyric acid benzyl ester
  参考文献：
  名称：

  RNA Modified Uridines VII: Chemical Synthesis and Initial Analysis of tRNA D-Loop Oligomers with Tandem Modified Uridines

  摘要：

  The first chemical synthesis of oligoribonucleotides with adjacent and significantly different modified uridines, the hydrophobic dihydrouridine, D, and the hydrophilic 3-[3-(S)-amino-3-carboxypropyl]-uridine, (acp)U-3, is reported. The trimers Dp-acp(3)UpA, Up-acp(3)UpA, DpUpA and UpUpA, and the dimer Dp-acp(3)U were synthesized and initial structural analysis performed. The synthesis included a combination of protecting groups that is generally applicable to oligonucleotide syntheses in combination with various 2'OH protecting groups. The protecting groups did not cause racemization of the amino acid residue of (acp)3U during deprotection. The assignment of all H-1 NMR resonances of modified nucleoside-containing oligoribonucleotides includes heteronuclear one and two dimensional NMR.

  DOI：

  10.1080/15257779508014659
• 作为产物：
  描述：

  1,3二氯-1,1,3,3-四异丙基二硅氧烷 、 (S)-2-Benzyloxycarbonylamino-4-[3-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-butyric acid benzyl ester 在 吡啶 作用下， 反应 3.0h， 以72%的产率得到(S)-2-Benzyloxycarbonylamino-4-[3-((2R,3R,3aS,9aR)-3-hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-butyric acid benzyl ester
  参考文献：
  名称：

  RNA Modified Uridines VII: Chemical Synthesis and Initial Analysis of tRNA D-Loop Oligomers with Tandem Modified Uridines

  摘要：

  The first chemical synthesis of oligoribonucleotides with adjacent and significantly different modified uridines, the hydrophobic dihydrouridine, D, and the hydrophilic 3-[3-(S)-amino-3-carboxypropyl]-uridine, (acp)U-3, is reported. The trimers Dp-acp(3)UpA, Up-acp(3)UpA, DpUpA and UpUpA, and the dimer Dp-acp(3)U were synthesized and initial structural analysis performed. The synthesis included a combination of protecting groups that is generally applicable to oligonucleotide syntheses in combination with various 2'OH protecting groups. The protecting groups did not cause racemization of the amino acid residue of (acp)3U during deprotection. The assignment of all H-1 NMR resonances of modified nucleoside-containing oligoribonucleotides includes heteronuclear one and two dimensional NMR.

  DOI：

  10.1080/15257779508014659