7-(2'-Desoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2-methylthio-7H-pyrrolo<2,3-d>pyrimidin | 98891-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 7-(2'-Desoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2-methylthio-7H-pyrrolo<2,3-d>pyrimidin
• 英文别名: 7-(2'-Desoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin；(2R,3S,5R)-2-(hydroxymethyl)-5-(4-methoxy-2-methylsulfanylpyrrolo[2,3-d]pyrimidin-7-yl)oxolan-3-ol
• CAS: 98891-39-5
• 化学式: C₁₃H₁₇N₃O₄S
• 分子量: 311.362
• InChiKey: HTAVSRFFGJPAMT-IVZWLZJFSA-N

物化性质

• 沸点：
  625.3±65.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  7-(2'-Desoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2-methylthio-7H-pyrrolo<2,3-d>pyrimidin 在 copper(l) iodide 、 四(三苯基膦)钯 吡啶 、 4-二甲氨基吡啶 、 ammonium hydroxide 、 N-碘代丁二酰亚胺 、 甲酸 、 三正丁基氢锡 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 7-TFA-AP-7-DEAZA-双脱氧鸟苷
  参考文献：
  名称：

  Confalone, Pat. N., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 1, p. 31 - 46

  摘要：

  DOI：
• 作为产物：
  描述：

  7-[2'-Desoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-4-methoxy-2-methylthio-7H-pyrrolo[2,3-d]pyrimidin 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以570 mg的产率得到7-(2'-Desoxy-β-D-erythro-pentofuranosyl)-4-methoxy-2-methylthio-7H-pyrrolo<2,3-d>pyrimidin
  参考文献：
  名称：

  7-Deaza-2′-deoxyinosine: A Stable Nucleoside with the Ambiguous Base Pairing Properties of 2′-Deoxyinosine

  摘要：

  The base pairing ambiguity of 7-deaza-2'-deoxyinosine (c(7)Id, 2) was studied and was found to be the same as that of 2'-deoxyinosine. The duplex stability decreases in the order [d(c(7)I-C) > d(c(7)I-A) > d(c(7)I-T) > d(c(7)I-G)]. Modified nucleosides were used to probe the various base pair motifs which were the same for dl and c(7)I(d). The 7-deazapurine nucleoside (2) is extremely stable against acid or base. As oligonucleotides can be prepared using phosphoramidite chemistry and DNA is accessible by enzymic polymerisation of the triphosphate of 2, the latter can be used as an universal nucleoside for the sequencing of DNA by chemical degradation and is otherwise a facile substitute of 2'-deoxyinosine when stability in acidic or alkaline solution is required.

  DOI：

  10.1080/15257779908043087

文献信息

• Total synthesis of 7-iodo-2′,3′-dideoxy-7-deazapurine nucleosides, key intermediates in the preparation of reagents for the automated sequencing of DNA
  作者：Anthony J. Cocuzza

  DOI：10.1016/s0040-4039(00)80417-7

  日期：1988.1

  Practical syntheses of 7-iodo-2′,3′-dideoxy-7-deazaadenosine and 7-iodo-2′,3′-dideoxy-7-deazaguanosine are described. These iodonucleosides can be converted into fluorescence-tagged chain-terminating substrates for DNA polymerases.

  描述了7-碘-2'，3'-二脱氧-7-脱氮杂腺苷和7-碘-2'，3'-二脱氧-7-脱氮鸟苷的实用合成。这些碘核苷可以转化为DNA聚合酶的荧光标记的链终止底物。
• Seela, Frank; Menkhoff, Sabine, Liebigs Annalen der Chemie, 1985, # 7, p. 1360 - 1366
  作者：Seela, Frank、Menkhoff, Sabine

  DOI：——

  日期：——
• COCUZZA, ANTHONY J., TETRAHEDRON LETT., 29,(1988) N 33, C. 4061-4064
  作者：COCUZZA, ANTHONY J.

  DOI：——

  日期：——
• Confalone, Pat. N., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 1, p. 31 - 46
  作者：Confalone, Pat. N.

  DOI：——

  日期：——
• 7-Deaza-2′-deoxyinosine: A Stable Nucleoside with the Ambiguous Base Pairing Properties of 2′-Deoxyinosine
  作者：Frank Seela、Cathrin Mittelbach

  DOI：10.1080/15257779908043087

  日期：1999.3

  The base pairing ambiguity of 7-deaza-2'-deoxyinosine (c(7)Id, 2) was studied and was found to be the same as that of 2'-deoxyinosine. The duplex stability decreases in the order [d(c(7)I-C) > d(c(7)I-A) > d(c(7)I-T) > d(c(7)I-G)]. Modified nucleosides were used to probe the various base pair motifs which were the same for dl and c(7)I(d). The 7-deazapurine nucleoside (2) is extremely stable against acid or base. As oligonucleotides can be prepared using phosphoramidite chemistry and DNA is accessible by enzymic polymerisation of the triphosphate of 2, the latter can be used as an universal nucleoside for the sequencing of DNA by chemical degradation and is otherwise a facile substitute of 2'-deoxyinosine when stability in acidic or alkaline solution is required.