[(2R,3S,5R)-3-hydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl acetate | 229326-12-9

• 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: [(2R,3S,5R)-3-hydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl acetate
• CAS: 229326-12-9
• 化学式: C₁₂H₁₄N₄O₅
• 分子量: 294.267
• InChiKey: CSZMKQXMURKSRQ-DJLDLDEBSA-N

物化性质

• 沸点：
  682.9±55.0 °C(Predicted)
• 密度：
  1.73±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：
  0.5
• 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：

  [(2R,3S,5R)-3-hydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl acetate 在 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 21.0h， 生成 [(2S,5R)-5-(6-氧代-3,6-二氢-9H-嘌呤-9-基)四氢-2-呋喃基]甲基乙酸酯
  参考文献：
  名称：

  Lipase-catalyzed protection of the hydroxy groups of the nucleosides inosine and 2′-deoxyinosine: A new chemoenzymatic synthesis of the antiviral drug 2′,3′-dideoxyinosine

  摘要：

  The selective acylation of the hydroxy groups of the nucleosides inosine la and 2'-deoxyinosine Ib has been achieved in the presence of Candida antarctica and Pseudomonas sp. lipases in organic solvents; starting from the 5'-acetyl derivative of 2'-deoxyinosine, compound 5a, an efficient chemoenzymatic synthesis of the antiviral drug 2',3'-dideoxyinosine 1c has been achieved, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00228-0
• 作为产物：
  描述：

  2'-脱氧腺苷 在 吡啶 、 Candida antarctica lipase 、 adenosine deaminase 作用下， 反应 21.0h， 生成 [(2R,3S,5R)-3-hydroxy-5-(6-oxo-1H-purin-9-yl)oxolan-2-yl]methyl acetate
  参考文献：
  名称：

  Lipase-catalyzed protection of the hydroxy groups of the nucleosides inosine and 2′-deoxyinosine: A new chemoenzymatic synthesis of the antiviral drug 2′,3′-dideoxyinosine

  摘要：

  The selective acylation of the hydroxy groups of the nucleosides inosine la and 2'-deoxyinosine Ib has been achieved in the presence of Candida antarctica and Pseudomonas sp. lipases in organic solvents; starting from the 5'-acetyl derivative of 2'-deoxyinosine, compound 5a, an efficient chemoenzymatic synthesis of the antiviral drug 2',3'-dideoxyinosine 1c has been achieved, (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00228-0

文献信息

• Nucleosides and Nucleotides. 143. Synthesis of 5-Amino-4-imidazolecarboxamide (AICA) Deoxyribosides from Deoxyinosines and Their Conversion into 3-Deazapurine Derivatives.
  作者：Noriaki MINAKAWA、Yoshimasa SASABUCHI、Arihiro KIYOSUE、Naoshi KOJIMA、Akira MATSUDA

  DOI：10.1248/cpb.44.288

  日期：——

  An efficient and large scale chamical synthesis of 5-aminoimidazole-4-carboxamide (AICA) 2'-deoxyriboside (5a) and its 3'-deoxyriboside 5b is described. Treatment of 3', 5'-di-O-acetyl-N1-triphenylmethyl-2'-deoxyinosine (3a) with 5 N NaOH in EtOH, followed by anhydrous trifluoroacetic acid gave 5a in 59% yield from 2'-deoxyinosine (1a). AICA 3'-deoxyriboside (5b) was also obtained in a similar manner as for 5a in 73% yield from 3'-deoxyinosine (1b). Conversion of these AICA derivatives (5a, b) into 3-deazapurine derivatives (9a, b, 15a, b, 20a, b) is also described.

  描述了一种高效且大规模的5-氨基咪唑-4-氨基乙酸（AICA）2'-脱氧核糖苷（5a）及其3'-脱氧核糖苷（5b）的化学合成。将3', 5'-二-O-乙酰基-N1-三苯甲基-2'-脱氧腺苷（3a）用5 N氢氧化钠在乙醇中处理，随后用无水三氟乙酸处理，从2'-脱氧腺苷（1a）得到的5a的产率为59%。AICA 3'-脱氧核糖苷（5b）也以类似的方式从3'-脱氧腺苷（1b）获得，产率为73%。还描述了将这些AICA衍生物（5a、b）转化为3-去氨嘌呤衍生物（9a、b，15a、b，20a、b）。