2-{9-[(3aR,4R,6R,6aR)-2,2-Dimethyl-6-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-propionic acid ethyl ester | 139574-42-8

• 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: 2-{9-[(3aR,4R,6R,6aR)-2,2-Dimethyl-6-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-propionic acid ethyl ester
• CAS: 139574-42-8
• 化学式: C₂₃H₃₂N₄O₇
• 分子量: 476.53
• InChiKey: MDJZHMJEDMVULU-PSZXWEALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  34.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  116.05
• 氢给体数：
  0.0
• 氢受体数：
  11.0

反应信息

• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 palladium on activated charcoal 氢气 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 5.0~85.0 ℃ 、405.3 kPa 条件下， 反应 63.17h， 生成 2-{9-[(3aR,4R,6R,6aR)-2,2-Dimethyl-6-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-9H-purin-6-yl}-propionic acid ethyl ester
  参考文献：
  名称：

  Design and Synthesis of a New Fluorescent Tricyclic Nucleoside, 3-.beta.-D-Ribofuranosylpyrazolo[3,2-i]purine

  摘要：

  The novel nucleoside, 3-beta-D-ribofuranosylpyrazolo[3,2-i]purine, has been prepared in seven steps from a fully protected 6-chloropurine derivative including a one-step reaction for the preparation of an ethyl 3-beta-D-ribofuranosylpyrazolo[3,2-i]purine derivative from 6-enamino purine and hydrazine. The mechanism for the preparation of 9-ethyl-substituted pyrazolo[3,2-i]purines was elucidated. First, the hydrazino moiety of 6-enamino purine attacks at the C-6 carbon of the purine ring to give a spiro intermediate; this is followed by ring opening and cyclization. The new tricyclic nucleoside exhibited stronger fluorescence than that of 1,N6-ethenoadenosine. Also, the compound and the 9-bromo-substituted pyrazolo[3,2-i]purine nucleoside showed cytotoxic activities against human leukemia CCRF-HSB-2 cells in culture.

  DOI：

  10.1021/jo00085a046

文献信息

• Synthesis and mechanism of formation of novel tricyclic nucleosides, 3-β-d-ribofuranosylpyrazolo[3,2-purine derivatives, by a one-step reaction of 6-enaminopurine with hydrazine
  作者：Norimitsu Hamamichi

  DOI：10.1016/0040-4039(91)80121-l

  日期：1991.12

  Ethyl 3-β-D-ribofuranosylpyrazolo[3,2-purine-9-carboxylate (8) has been prepared from a fully protected 6-chloropurine derivative in four steps including a one-step reaction for the preparation of 3-β-D-ribofuranosyl-[3,2-purine derivative 5 (by 6-enaminopurine and hydrazine, and the mechanism of formation of 5 is discussed.

  3-β-D-呋喃呋喃糖基吡唑并[3,2-嘌呤-9-羧酸酯]（8）是由受完全保护的6-氯嘌呤衍生物分四步制备的，包括一步反应制备3-β-D -核呋喃糖基-[3，2-嘌呤衍生物5（由6-烯氨基嘌呤和肼），并讨论了5的形成机理。