2,4-dichloro-7-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine | 1053228-30-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4-dichloro-7-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine
• CAS: 1053228-30-0
• 化学式: C₂₇H₂₂Cl₂FN₃O₅
• 分子量: 558.393
• InChiKey: YXLWQDWHKVRCNP-PWRODBHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.86
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  92.54
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2,4-dichloro-7-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine 在 氨 作用下， 以 甲醇 为溶剂， 以80%的产率得到2-chloro-7-(2-deoxy-β-D-erythro-pentofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  Fluorinated 7-Deazapurine 2′-Deoxyribonucleosides: Modification At The Nucleobase And The Sugar Moiety

  摘要：

  7-Deaza-7-fluoro-purine 2'-deoxynucleosides as well as 2'-deoxy-2'-fluoroarabinofuranosyl nucleosides 1-8 were synthesized. The fluorine atom was introduced on the base level with Seleqfluor Nucleobase-anion glycosylation was then employed to form the nucleosides. Properties of the fluorine compounds were studied in solution and in solid state. Compound 4a was incorporated into oligonucleotides where the stabilizing effect was observed.

  DOI：

  10.1080/15257770701490357
• 作为产物：
  描述：

  2,4-二氯-5-氟-7h-吡咯并[2,3-d]嘧啶 、 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythropentofuranosyl chloride 在 氢氧化钾 、 三(3,6-二氧杂庚基)胺 作用下， 以 乙腈 为溶剂， 以64%的产率得到2,4-dichloro-7-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine
  参考文献：
  名称：

  Fluorinated 7-Deazapurine 2′-Deoxyribonucleosides: Modification At The Nucleobase And The Sugar Moiety

  摘要：

  7-Deaza-7-fluoro-purine 2'-deoxynucleosides as well as 2'-deoxy-2'-fluoroarabinofuranosyl nucleosides 1-8 were synthesized. The fluorine atom was introduced on the base level with Seleqfluor Nucleobase-anion glycosylation was then employed to form the nucleosides. Properties of the fluorine compounds were studied in solution and in solid state. Compound 4a was incorporated into oligonucleotides where the stabilizing effect was observed.

  DOI：

  10.1080/15257770701490357

文献信息

• 7‐Halogenated 7‐Deazapurine 2′‐Deoxyribonucleosides Related to 2′‐Deoxyadenosine, 2′‐Deoxyxanthosine, and 2′‐Deoxyisoguanosine: Syntheses and Properties
  作者：Frank Seela、Kuiying Xu

  DOI：10.1002/hlca.200890117

  日期：2008.6

  A series of 7-fluorinated 7-deazapurine 2′-deoxyribonucleosides related to 2′-deoxyadenosine, 2′-deoxyxanthosine, and 2′-deoxyisoguanosine as well as intermediates 4b–7b, 8, 9b, 10b, and 17b were synthesized. The 7-fluoro substituent was introduced in 2,6-dichloro-7-deaza-9H-purine (11a) with Selectfluor (Scheme 1). Apart from 2,6-dichloro-7-fluoro-7-deaza-9H-purine (11b), the 7-chloro compound 11c

  合成了一系列与2'-脱氧腺苷，2'-脱氧黄嘌呤和2'-脱氧异鸟苷相关的7-氟化7-脱氮嘌呤2'-脱氧核糖核苷以及中间体4b - 7b， 8、9b ，10b和17b。将7-氟取代基与Selectfluor一起引入2，6-二氯-7-脱氮基-9 H-嘌呤（11a）中（方案1）。除了2，6-二氯-7-氟-7-脱氮基-9 H-嘌呤（11b）以外，还形成了副产物7-氯化合物11c。混合物11b / 11c用于糖基化反应；在未保护的核苷水平上从7-氯化合物中分离7-氟。其他卤素取代基与N-卤代琥珀酰亚胺（11a 11c – 11e）一起引入。碱基碱基阴离子糖基化提供了核苷中间体13a - 13e（方案2）。从相应的MeO化合物17b和17c或18分别获得7-氟-和7-氯-7-脱氮基2'-脱氧黄嘌呤核苷5b和5c（方案6）。通过光化学诱导的亲核取代反应由2-氯-7-氟-7-脱氮基-2'-脱氧腺苷6b制备2