9-<2-deoxy-β-D-erythro-pentofuranosyl>-6-methoxy-9H-purine | 37109-88-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-<2-deoxy-β-D-erythro-pentofuranosyl>-6-methoxy-9H-purine
• 英文别名: 9-(2-deoxy-β-D-erythro-pentofuranosyl)-6-methoxypurine；Inosine,2'-deoxy-6-O-methyl-；(2R,3S,5R)-2-(hydroxymethyl)-5-(6-methoxypurin-9-yl)oxolan-3-ol
• CAS: 37109-88-9
• 化学式: C₁₁H₁₄N₄O₄
• 分子量: 266.257
• InChiKey: OKUCPECQZYJFRT-XLPZGREQSA-N

物化性质

• 沸点：
  565.5±60.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  9-<2-deoxy-β-D-erythro-pentofuranosyl>-6-methoxy-9H-purine 以 盐酸 、 水 为溶剂， 生成 6-甲氧基嘌呤
  参考文献：
  名称：

  6-取代的9-（2-脱氧-β-d-异戊-呋喃呋喃糖基）嘌呤及其9-（1-烷氧乙基）对应部分的酸性水解：动力学和机理。1个

  摘要：

  已经在不同浓度的氧离子下测量了几种6-取代的9-（2-脱氧-β-D-赤-戊呋喃糖基）嘌呤和9-（1-烷氧基乙基）嘌呤的水解速率常数。解释了改变烷氧基极性性质对未取代的9-（1-烷氧基乙基）嘌呤水解的影响，这表明该反应是通过质子化碱部分的限速离去并伴随形成一个烷氧基乙基氧碳鎓离子。通过比较6-取代基对这些化合物及其9-（1-烷氧基乙基）反应剂的反应性的影响，将相同的机理应用于9-（2-脱氧-β-D-赤-戊呋喃糖基）嘌呤的水解。 -部分。当2'-脱氧腺苷水解后进行1 H NMR光谱。

  DOI：

  10.1016/s0040-4020(01)90052-3
• 作为产物：
  描述：

  2'-脱氧腺苷 在 吡啶 、 Dowex 1*2 (OH^-) 作用下， 反应 24.0h， 生成 9-<2-deoxy-β-D-erythro-pentofuranosyl>-6-methoxy-9H-purine
  参考文献：
  名称：

  Miles, Robert W.; Samano, Vicente; Robins, Morris J., Journal of the American Chemical Society, 1995, vol. 117, # 22, p. 5951 - 5957

  摘要：

  DOI：

文献信息

• Purine nucleoside synthesis from uridine using immobilised Enterobacter gergoviae CECT 875 whole cells
  作者：J.A Trelles、M Fernández、E.S Lewkowicz、A.M Iribarren、J.V Sinisterra

  DOI：10.1016/s0040-4039(03)00225-9

  日期：2003.3

  Biocatalysed purine nucleoside synthesis was carried out using immobilised Enterobacter gergoviae CECT 875. Similar yields (80-95%) in adenosine were obtained with both free and immobilised cells though in the last case a long reaction time was necessary. The immobilised cells can be reused at least for more than 30 times without significant loss of enzymatic activity. The immobilised biocatalyst in agarose is active in the synthesis of unnatural nucleosides. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of 6-Substituted Purine N⁷-(2-Deoxy-β-D-Ribonucleosides) via Anion Glycosylation and Anomerization During the N⁷/N⁹-Glycosyl Transfer
  作者：Frank Seela、Holger Winter

  DOI：10.1080/15257779508014658

  日期：1995.2

  The synthesis of the 7-(2-deoxy-beta-D-erythro-pentofuranosyl) adenine (Ib) as well as the corresponding hypoxanthine- and purine nucleosides 3 and 4 is described employing the stereoselective nucleobase anion glycosylation. The N-7/N-9- isomer distribution of the 6-substituted purine (2-deoxyribonucleosides) depends on 6-substituent. Glycosyl transfer of 8a resulted in anomerization and yielded a mixture of the anomeric 6-methoxypurine N-9-(2-deoxy-D-ribonucleosides) 7a/7d. The preferred glycosylic bond conformation of purine N-7-(2-deoxyribonucleosides) is anti.
• Miles, Robert W.; Samano, Vicente; Robins, Morris J., Journal of the American Chemical Society, 1995, vol. 117, # 22, p. 5951 - 5957
  作者：Miles, Robert W.、Samano, Vicente、Robins, Morris J.

  DOI：——

  日期：——
• Acidic hydrolysis of 6-substituted 9-(2-deoxy-β--- pentofuranosyl) purines and their 9-(1-alkoxyethyl) counter-parts: kinetics and mechanism.1
  作者：Mikko OivanXXXn、Harri Lönnberg、Xiao-xiong Zhou、Jyoti Chattopadhyaya

  DOI：10.1016/s0040-4020(01)90052-3

  日期：1987.1

  The rate constants for the hydrolysis of several 6-substituted 9-(2-deoxy-β-D-erythro-pentofuranosyl)purines and 9-(1-alkoxyethyl) purines have been measured at different concentrations of oxonium ion. The effects that varying the polar nature of the alkoxy group exerts on the hydrolysis of unsubstituted 9-(1-alkoxyethyl) purines are interpreted to indicate that the reaction proceeds by a rate-limiting

  已经在不同浓度的氧离子下测量了几种6-取代的9-（2-脱氧-β-D-赤-戊呋喃糖基）嘌呤和9-（1-烷氧基乙基）嘌呤的水解速率常数。解释了改变烷氧基极性性质对未取代的9-（1-烷氧基乙基）嘌呤水解的影响，这表明该反应是通过质子化碱部分的限速离去并伴随形成一个烷氧基乙基氧碳鎓离子。通过比较6-取代基对这些化合物及其9-（1-烷氧基乙基）反应剂的反应性的影响，将相同的机理应用于9-（2-脱氧-β-D-赤-戊呋喃糖基）嘌呤的水解。 -部分。当2'-脱氧腺苷水解后进行1 H NMR光谱。