2,2'-Anhydro-1-(3',5'-di-O-acetyl-β-D-arabinofuranosyl)-5,6-dihydrothymine | 191224-00-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2'-Anhydro-1-(3',5'-di-O-acetyl-β-D-arabinofuranosyl)-5,6-dihydrothymine
• 英文别名: [(2R,4R,5R,6S)-5-acetyloxy-11-methyl-10-oxo-3,7-dioxa-1,9-diazatricyclo[6.4.0.02,6]dodec-8-en-4-yl]methyl acetate
• CAS: 191224-00-7
• 化学式: C₁₄H₁₈N₂O₇
• 分子量: 326.306
• InChiKey: HXOSLFURQZZSIJ-OJGPCYDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,2'-Anhydro-1-(3',5'-di-O-acetyl-β-D-arabinofuranosyl)-5,6-dihydrothymine 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以6%的产率得到1-(3',5'-Di-O-acetyl-2'-chloro-2'-deoxy-β-D-ribofuranosyl)-5,6-dihydrothymine
  参考文献：
  名称：

  Unprecedented chlorination of 2,2′-anhydro-5,6-dihydropyrimidine nucleosides during DDQ oxidation

  摘要：

  Chloride ion, derived from 2,3-dichloro-5,6-dicyanohydroquinone (DDHQ), was found to participate in opening of the 2,2'-anhydro bond of 5,6-dihydropyrimidine nucleosides, but not their 5,6-unsaturated counterparts. The increased basicity of the nucleosidic nitrogen is believed to be a factor in this unprecedented reaction. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00727-2
• 作为产物：
  描述：

  2,2'-Anhydro-1-β-D-arabinofuranosyl-5,6-dihydrothymine 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以100%的产率得到2,2'-Anhydro-1-(3',5'-di-O-acetyl-β-D-arabinofuranosyl)-5,6-dihydrothymine
  参考文献：
  名称：

  Diastereomeric 5,6-Dihydrothymidines. Preparation, Stereochemical Assignments, and MnO2 Oxidation Studies of Thymidines

  摘要：

  A useful method for the stereospecific synthesis of beta-thymidine and beta-5,6-dihydrothymidine nucleosides is described. Condensation of methyl 2-formylpropionate and methyl methacrylate with oxazolines 8 furnished the corresponding 2,2'-anhydrothymidine 11 and a 2:1 diastereomeric mixture of 2,2'-anhydro-5,6-dihydrothymidine 10, respectively. While DDQ oxidation of 10 furnished 11, active MnO2 resulted in a selective dehydrogenation hitherto unreported in nucleoside chemistry. The minor diasteromer 10b was quantitatively converted to 11, leaving 10a unchanged. A plausible explanation for this selectivity was based on the stereochemistry at C5 which was determined by one-dimensional NOE studies.

  DOI：

  10.1021/jo00115a026