| 142742-66-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• CAS: 142742-66-3
• 化学式: C₁₄H₁₅F₃N₂O₉S
• 分子量: 444.342
• InChiKey: HNLFDJQASSJANN-PNHWDRBUSA-N

反应信息

• 作为反应物：
  描述：

  在 sodium tetrahydroborate 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以85%的产率得到2',3'-O-isopropylidene-O^5',6-methanouridine
  参考文献：
  名称：

  O^5′,6-Methanocytidine — Synthesis, Conformational Properties and Deamination by Cytidine Deaminase

  摘要：

  The synthesis of O-5',O-6-methanocytidine (4), a pyrimidine nucleoside restricted to the anti conformation, is described. Molecular modeling studies suggest that 4 is more flexible than conventional cyclonucleosides because of its larger-than-usual bridging system and that it can exist in a number of low energy conformations where the glycosyl rotation angles (chi) cover an similar to 80 degrees segment of the anti range. However, while both N-type (C2'-exo) and S-type (C3'-exo) sugar puckerings are possible, none of the low energy conformers adopt the C3'-endo or C2'-endo puckering modes generally seen for unconstrained nucleosides. The lowest energy conformer predicted for 4 (chi = -152 degrees, gamma = 73 degrees, P = 206 degrees) is similar to the X-ray structure of a related compound, namely 5-hydroxy-O-5',O-6-methanouridine (12, chi = -138 degrees, gamma = 63 degrees, P = 200 degrees). In solution, NMR evidence suggests an equilibrium between C2'-exo and C3'-exo puckerings for 4, and CD evidence suggests an average glycosyl rotation angle (chi) of around -160 degrees. O-5',O-6-Methano-cytidine (4) is slowly deaminated by crude cytidine deaminase from mouse liver to give O-5',O-6-methanouridine (3). Assuming that 4 interacts with the normal active site, it is concluded that cytidine deaminase from that particular source requires its ordinary substrates to adopt the anti conformation.

  DOI：

  10.1080/15257779408013214
• 作为产物：
  描述：

  Acetic acid 6-acetoxymethyl-1-((3aR,4R,6R,6aR)-6-acetoxymethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl ester 在 sodium hydroxide 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成
  参考文献：
  名称：

  O^5′,6-Methanocytidine — Synthesis, Conformational Properties and Deamination by Cytidine Deaminase

  摘要：

  The synthesis of O-5',O-6-methanocytidine (4), a pyrimidine nucleoside restricted to the anti conformation, is described. Molecular modeling studies suggest that 4 is more flexible than conventional cyclonucleosides because of its larger-than-usual bridging system and that it can exist in a number of low energy conformations where the glycosyl rotation angles (chi) cover an similar to 80 degrees segment of the anti range. However, while both N-type (C2'-exo) and S-type (C3'-exo) sugar puckerings are possible, none of the low energy conformers adopt the C3'-endo or C2'-endo puckering modes generally seen for unconstrained nucleosides. The lowest energy conformer predicted for 4 (chi = -152 degrees, gamma = 73 degrees, P = 206 degrees) is similar to the X-ray structure of a related compound, namely 5-hydroxy-O-5',O-6-methanouridine (12, chi = -138 degrees, gamma = 63 degrees, P = 200 degrees). In solution, NMR evidence suggests an equilibrium between C2'-exo and C3'-exo puckerings for 4, and CD evidence suggests an average glycosyl rotation angle (chi) of around -160 degrees. O-5',O-6-Methano-cytidine (4) is slowly deaminated by crude cytidine deaminase from mouse liver to give O-5',O-6-methanouridine (3). Assuming that 4 interacts with the normal active site, it is concluded that cytidine deaminase from that particular source requires its ordinary substrates to adopt the anti conformation.

  DOI：

  10.1080/15257779408013214