1,5-anhydro-3-O-benzoyl-6-O-monomethoxytrityl-2-deoxy-2-(uracil-1-yl)-D-altro-hexitol | 215959-66-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,5-anhydro-3-O-benzoyl-6-O-monomethoxytrityl-2-deoxy-2-(uracil-1-yl)-D-altro-hexitol
• 英文别名: [(2R,3S,4S,5R)-5-(2,4-dioxopyrimidin-1-yl)-3-hydroxy-2-[[(4-methoxyphenyl)-diphenylmethoxy]methyl]oxan-4-yl] benzoate
• CAS: 215959-66-3
• 化学式: C₃₇H₃₄N₂O₈
• 分子量: 634.686
• InChiKey: GSJJXHOYIOJPEP-CUTZNAIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  47.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  129.08
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-3-O-benzoyl-6-O-monomethoxytrityl-2-deoxy-2-(uracil-1-yl)-D-altro-hexitol 、 alkaline earth salt of/the/ methylsulfuric acid 以94%的产率得到2-(Uracil-1-yl)-3-O-benzoyl-2-deoxy-4-O-[N,N-diisopropyl(2-cyanoethyl)]phosphoramidite-6-O-monomethoxytrityl-D-altritol
  参考文献：
  名称：

  1,5-Anhydro-2-Deoxy-D-Altritol Oligonucleotides as Conformationally Restricted Analogues of Rna

  摘要：

  As part of a project concerning the investigation of new hexitol nucleic acids (HNA), the 1,5-anhydro-2-deoxy-D-altritol nucleoside building blacks with a uracil, cytosine, adenine and guanine base moiety were synthesized. The uracil analogue was used for the automated synthesis of corresponding oligonucleotides. Hybridization capabilities of these altritol nucleic acids (ANA) are illustrated by the Tm values obtained for the (a(h)U)(13)/(dA)(13) duplex.

  DOI：

  10.1080/07328319808004682
• 作为产物：
  描述：

  1-((4aR,7R,8S,8aS)-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-1H-pyrimidine-2,4-dione 在 2,4,6-三甲基吡啶 、 silver nitrate 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1,5-anhydro-3-O-benzoyl-6-O-monomethoxytrityl-2-deoxy-2-(uracil-1-yl)-D-altro-hexitol
  参考文献：
  名称：

  1,5-Anhydro-2-Deoxy-D-Altritol Oligonucleotides as Conformationally Restricted Analogues of Rna

  摘要：

  As part of a project concerning the investigation of new hexitol nucleic acids (HNA), the 1,5-anhydro-2-deoxy-D-altritol nucleoside building blacks with a uracil, cytosine, adenine and guanine base moiety were synthesized. The uracil analogue was used for the automated synthesis of corresponding oligonucleotides. Hybridization capabilities of these altritol nucleic acids (ANA) are illustrated by the Tm values obtained for the (a(h)U)(13)/(dA)(13) duplex.

  DOI：

  10.1080/07328319808004682

文献信息

• Synthesis of protected D-altritol nucleosides as building blocks for oligonucleotide synthesis
  作者：Brigitte Allart、Roger Busson、Jef Rozenski、Arthur Van Aerschot、Piet Herdewijn

  DOI：10.1016/s0040-4020(99)00287-2

  日期：1999.5

  D-Altritol nucleosides with an adenine and uracil base moiety were obtained by nucleophilic opening of the epoxide ring of 1,5:2,3-dianhydro-4,6-O-benzylidene-D-allitol using the sodium salt of the above mentioned bases. The use of a 2-trimethylsilylethyl protecting group for the O6-function of the guanine base offers a useful compromise between stability and acceptable alkylation yields of the N9-position

  与腺嘌呤和尿嘧啶碱基部分d-阿卓糖醇核苷由1,5-环氧化物环的亲核开得到：2,3-二脱水-4,6- ø -亚苄基- d-蒜糖醇使用上述提到的钠盐基地。将2-三甲基甲硅烷基乙基保护基用于鸟嘌呤碱基的O 6-官能团在鸟嘌呤碱基的稳定性和N 9-位置可接受的烷基化产率之间提供了有用的折衷方案。从尿嘧啶同源物开始合成胞嘧啶核苷。3'-羟基官能团被苯甲酰基保护。