4-氯-5-碘-7-(beta-D-呋喃核糖基)-7H-吡咯并[2,3-d]嘧啶-2-胺 | 873792-94-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 吡咯并嘧啶核苷和核苷酸
• 中文名称: 4-氯-5-碘-7-(beta-D-呋喃核糖基)-7H-吡咯并[2,3-d]嘧啶-2-胺
• 英文名称: 2-amino-4-chloro-5-iodo-7-{β-D-ribofuranosyl}-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: (2R,3R,4S,5R)-2-(2-amino-4-chloro-5-iodopyrrolo[2,3-d]pyrimidin-7-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 873792-94-0
• 化学式: C₁₁H₁₂ClIN₄O₄
• 分子量: 426.598
• InChiKey: RYFLMNAAVNGVRF-KQYNXXCUSA-N

物化性质

• 熔点：
  180 °C(Solv: methanol (67-56-1))
• 沸点：
  751.2±70.0 °C(Predicted)
• 密度：
  2.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-氯-5-碘-7-(beta-D-呋喃核糖基)-7H-吡咯并[2,3-d]嘧啶-2-胺 在 sodium hydroxide 作用下， 以76%的产率得到7-deaza-7-iodoguanosine
  参考文献：
  名称：

  7-DEAZAPURIN-2,6-DIAMINE AND 7-DEAZAGUANINE: SYNTHESIS AND PROPERTY OF 7-SUBSTITUTED NUCLEOSIDES AND OLIGONUCLEOTIDES

  摘要：

  The synthesis of 7-substituted 7-deazaguanine and 7-deazaadenine ribonucleosides 1-2, the incorporation of 3a-d into oligonucleotides, and the stability of the corresponding duplexes and base discrimination are described. The pK(a), values of 3 - 4 are determined.

  DOI：

  10.1081/ncn-200060319
• 作为产物：
  描述：

  4-氯-5-碘-1H-吡咯并[2,3-d]嘧啶-2-胺 在 氢氧化钾 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 4-氯-5-碘-7-(beta-D-呋喃核糖基)-7H-吡咯并[2,3-d]嘧啶-2-胺
  参考文献：
  名称：

  7-DEAZAPURIN-2,6-DIAMINE AND 7-DEAZAGUANINE: SYNTHESIS AND PROPERTY OF 7-SUBSTITUTED NUCLEOSIDES AND OLIGONUCLEOTIDES

  摘要：

  The synthesis of 7-substituted 7-deazaguanine and 7-deazaadenine ribonucleosides 1-2, the incorporation of 3a-d into oligonucleotides, and the stability of the corresponding duplexes and base discrimination are described. The pK(a), values of 3 - 4 are determined.

  DOI：

  10.1081/ncn-200060319

文献信息

• 7-Functionalized 7-Deazapurine Ribonucleosides Related to 2-Aminoadenosine, Guanosine, and Xanthosine:  Glycosylation of Pyrrolo[2,3-<i>d</i>]pyrimidines with 1-<i>O</i>-Acetyl-2,3,5-tri-<i>O</i>-benzoyl-<scp>d</scp>-ribofuranose
  作者：Frank Seela、Xiaohua Peng

  DOI：10.1021/jo0516640

  日期：2006.1.1

  The Silyl-Hilbert-Johnson reaction as well as the nucleobase-anion glycosylation of a series of 7-deazapurines has been investigated, and the 7-functionalized 7-deazapurine ribonucleosides were prepared. Glycosylation of the 7-halogenated 6-chloro-2-pivaloylamino-7-deazapurines 9b-d with 1-O-acetyl2,3,5-tri-O-benzOyl-D-ribofuranose (5) gave the beta-D-nucleosides 11b-d (73-75% yield), which were transformed to a number of novel 7-halogenated 7-deazapurine ribonucleosides (2b-d, 3b-d, and 4b-d) related to guanosine, 2-aminoadenosine, and xanthosine. 7-Alkynyl derivatives (2e-i, 3e-h, or 4g) have been prepared from the corresponding 7-iodonucleosides 2d, 3d, or 4d employing the palladium-catalyzed Sonogashira cross-coupling reaction. The 7-halogenated 2-amino-7-deazapurine ribonucleosides with a reactive 6-chloro substituent (18b-d) were synthesized in an alternative way using nucleobase-anion glycosylation performed on the 7-halogenated 2-arnino-6-chloro-7-deazapurines 13b-d with 5-0-[(1,1dimethylethyl)dimethylsilyl]-2,3-O-(1-methylethylidene)-alpha-D-ribofuranosyl chloride (17). Compounds 18b-d have been converted to the nucleosides 19b-d carrying reactive substituents in the pyrimidine moiety. Conformational analysis of selected nucleosides on the basis of proton coupling constants and using the program PSEUROT showed that these ribonucleosides exist in a preferred S conformation in solution.