1-(3,5-O-Benzylidene-2-deoxy-β-D-threo-pentofuranosyl)thymine | 142405-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1-(3,5-O-Benzylidene-2-deoxy-β-D-threo-pentofuranosyl)thymine
• CAS: 142405-93-4
• 化学式: C₁₇H₁₈N₂O₅
• 分子量: 330.34
• InChiKey: GPZVZXVSBZVCTK-QFBZGTDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  82.55
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  二乙基亚磷酰氯 、 1-(3,5-O-Benzylidene-2-deoxy-β-D-threo-pentofuranosyl)thymine 在 四氯化锡 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以84%的产率得到
  参考文献：
  名称：

  环状缩醛和缩酮的环扩大：七元核苷磷矿的一种方法。

  摘要：

  通过亚磷酸氯二乙酯与衍生自xylo-dT的3'，5'-缩醛或缩酮的反应制备了新型的七元核苷磷脂。提出了一种扩大环的机制，并通过从头算来为其提供支持。

  DOI：

  10.1021/ol7023899
• 作为产物：
  描述：

  Phenyl 2-deoxy-1-thio-α-D-threo-pentofuranoside 在 N-溴代丁二酰亚胺(NBS) 、 4 A molecular sieve 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.33h， 生成 1-(3,5-O-Benzylidene-2-deoxy-β-D-threo-pentofuranosyl)thymine
  参考文献：
  名称：

  Stereoselective Synthesis of 2'-Deoxy-.beta.-D-threo-pentofuranosyl Nucleosides by the NBS-Promoted Coupling Reaction of Thioglycosides with Silylated Heterocyclic Bases

  摘要：

  The NBS-promoted coupling reaction of phenyl 3,5-O-isopropylidene-2-deoxy-1-thio-alpha-D-threo-pentofuranoside (5e) with silylated pyrimidine bases was found to proceed in a highly stereoselective manner (alpha:beta = 1:24-0:1) to afford 2'-deoxy-beta-D-threo-pentofuranosyl pyrimidine nucleosides in satisfactory yields. The highly stereoselective outcome is thought to result from an in situ anomerization-type mechanism, in which intimate ionic intermediates would be in equilibrium and anomerize to the sterically preferable a form. A subsequent S(N)2 type attack to the intermediate will lead to the beta-nucleosides. By using this method, the synthesis of L-nucleosides, 1-(2-deoxy-beta-L-threo-pentofuranosyl)thymine and cytosine derivatives, was also demonstrated by starting from the L-enantiomer of the thioglycoside. On the other hand, the reaction with purine bases was accompanied by the production of undesirable N-7 regioisomers besides the desired N-9 products. The product distribution of the regioisomers was, however, proved to change with reaction time. For instance, a long reaction period allowed the thermodynamically stable N-9 isomers to be exclusively produced with moderate selectivity (alpha:beta = 1:2-1:4.8). The isolated yields of the 9-beta isomers after purification were acceptable for practical use.

  DOI：

  10.1021/jo00104a020

文献信息

• β-Selective synthesis of 2'-deoxynucleosides by the coupling of 2-deoxy-1-thio-D-threo-pentofuranosides with silylated thymine
  作者：Hideyuki Sugimura、Keiko Sujino、Kenji Osumi

  DOI：10.1016/s0040-4039(00)92229-9

  日期：1992.4

  The coupling of the 3,5-O-isopropylidene derivative of phenyl 2-deoxy-1-thio-D-threo-pentofuranoside with silylated thymine in the presence of N-bromosuccinimide yielded 1-(2-deoxy-beta-D-threo-pentofuranosyl)thymine with highly anomeric selectivity.